Organic electroluminescence device and novel compound

ABSTRACT

An organic electroluminescence device comprising:a cathode,an anode, andat least one organic layer disposed between the cathode and the anode, whereinat least one layer of the at least one organic layer comprises a compound represented by the following formulas (1-1) and (1-3) or a compound represented by the following formulas (1-2) and (1-3).

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a Continuation of U.S. patent applicationSer. No. 16/345,213, filed on Apr. 25, 2019, which is a U.S. NationalStage Application claiming the benefit of International Application No.PCT/JP2018/044792, filed on Dec. 5, 2018, which is a Continuation ofU.S. patent application Ser. No. 16/043,074, filed on Jul. 23, 2018 (nowU.S. Pat. No. 10,249,832, issued on Apr. 2, 2019), and U.S. patentapplication Ser. No. 16/201,984, filed on Jul. 23, 2018 (now U.S. Pat.No. 10,672,989, issued on Jun. 2, 2020), which claims the benefit ofpriority to Japanese Patent Application No. 2018-114580, filed Jun. 15,2018, and Japanese Patent Application No. 2017-234331, filed Dec. 6,2017, the disclosures of which are hereby incorporated by reference.

TECHNICAL FIELD

The invention relates to an organic electroluminescence device and anovel compound.

BACKGROUND ART

When a voltage is applied to an organic electroluminescence device(hereinafter may be referred to as an organic EL device), holes areinjected to an emitting layer from an anode and electrons are injectedto an emitting layer from a cathode. In the emitting layer, injectedholes and electrons are re-combined and excitons are formed.

An organic EL device comprises an emitting layer between the anode andthe cathode. Further, there may be a case where it has a stacked layerstructure comprising an organic layer such as a hole-injecting layer, ahole-transporting layer, an electron-injecting layer, anelectron-transporting layer, etc.

Patent Documents 1 to 3 disclose a compound used as a material for anorganic electroluminescence device.

RELATED ART DOCUMENTS Patent Documents

-   Patent Document 1: WO2013/077344-   Patent Document 2: U.S. Pat. No. 5,843,607-   Patent Document 3: WO2017/175690

SUMMARY OF THE INVENTION

An object of the invention is to provide an organic electroluminescencedevice having a high luminous efficiency and a novel compound that canbe used as a material for an organic electroluminescence device having ahigh luminous efficiency.

According to one aspect of the invention, an organic electroluminescencedevice comprising:

-   -   a cathode,    -   an anode, and    -   at least one organic layer disposed between the cathode and the        anode, wherein    -   at least one layer of the at least one organic layer comprises a        compound represented by the following formulas (1-1) and (1-3),        or a compound represented by the following formulas (1-2) and        (1-3):

-   -   wherein in the formulas (1-1), (1-2) and (1-3),    -   ring A is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms, a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms or a benzene ring represented by the following formula        (2);    -   two atomic bondings * in the formula (1-1) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   three atomic bondings * in the formula (1-2) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   one or more pairs of adjacent two or more of R₁ to R₁₆ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₁ to R₁₆ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄,        —COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro        group, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different;

-   -   wherein in the formula (2), at one of the two ring carbon atoms        indicated by * the atomic bonding extending from the benzene        ring B in the formula (1-1) or the formula (1-2) is bonded, and        at the other of the two ring carbon atoms indicated by *, the        atomic bonding extending from the benzene ring C in the formula        (1-3) is bonded;    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different; and    -   n is an integer of 1 or 2, and when n is 2, two R₁₇s may be the        same or different.

According to one aspect of the invention, an electronic apparatusprovided with the organic electroluminescence device is provided.

According to one aspect of the invention, a compound represented by thefollowing formulas (1-1) and (1-3), or a compound represented by thefollowing formulas (1-2) and (1-3) is provided:

-   -   wherein in the formulas (1-1), (1-2) and (1-3),    -   ring A is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms, a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms or a benzene ring represented by the following formula        (2);    -   two atomic bondings * in the formula (1-1) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   three atomic bondings * in the formula (1-2) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   one or more pairs of adjacent two or more of R₁ to R₁₆ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₁ to R₁₆ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄,        —COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro        group, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different; and    -   when the ring A is a benzene ring represented by the formula        (2), at least one of R₁ to R₁₇ is a substituted or unsubstituted        alkyl group including 1 to 50 carbon atoms, a substituted or        unsubstituted cycloalkyl group including 3 to 50 ring carbon        atoms, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms, or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms; or        at least one pair of adjacent two or more of R₁ to R₁₆ forms a        substituted or unsubstituted, saturated or unsaturated ring;

-   -   wherein in the formula (2), at one of the two ring carbon atoms        indicated by * the atomic bonding extending from the benzene        ring B in the formula (1-1) or the formula (1-2) is bonded, and        at the other of the two ring carbon atoms indicated by *, the        atomic bonding extending from the benzene ring C in the formula        (1-3) is bonded;    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different; and    -   n is an integer of 1 or 2, and when n is 2, two R₁₇s may be the        same or different.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a view showing a schematic configuration of one embodiment ofthe organic EL device of the invention, and

FIG. 2 is a view showing a schematic configuration of another embodimentof the organic EL device of the invention.

MODE FOR CARRYING OUT THE INVENTION

In the present specification, a hydrogen atom includes isomers differingin number of neutrons, i.e. protium, deuterium and tritium.

In the present specification, the number of “ring carbon atoms” meansthe number of carbon atoms among atoms constituting a ring itself of acompound in which atoms are bonded in the form of a ring (for example, amonocyclic compound, a fused ring compound, a cross-linked compound, acarbocyclic compound or a heterocyclic compound). When the ring issubstituted by a substituent, the carbon contained in the substituent isnot included in the number of ring carbon atoms. The same is applied tothe “ring carbon atoms” mentioned below, unless otherwise indicated. Forexample, a benzene ring includes 6 ring carbon atoms, a naphthalene ringincludes 10 ring carbon atoms, a pyridinyl group includes 5 ring carbonatoms, and a furanyl group includes 4 ring carbon atoms. When a benzenering or a naphthalene ring is substituted by an alkyl group as asubstituent, for example, the number of carbon atoms of the alkyl groupis not included in the number of ring carbon atoms. When a fluorene ringis bonded with a fluorene ring as a substituent (including aspirofluorene ring), for example, the number of carbon atoms of thefluorene ring as the substituent is not included in the number of ringcarbon atoms.

In the present specification, the number of “ring atoms” means thenumber of atoms constituting a ring itself of a compound having astructure in which atoms are bonded in the form of a ring (for example,monocycle, fused ring, ring assembly) (for example, a monocycliccompound, a fused ring compound, a cross-linked compound, a carbocycliccompound or a heterocyclic compound). It does not include atoms which donot form a ring (for example, a hydrogen atom which terminates theatomic bonding constituting a ring) or atoms contained in a substituentwhen the ring is substituted by the substituent. The same is applied tothe “ring atoms” mentioned below, unless otherwise indicated. Forexample, a pyridine ring includes 6 ring atoms, a quinazoline ringincludes 10 ring atoms, and a furan ring includes 5 ring atoms. Hydrogenatoms respectively bonded with a carbon atom of a pyridine ring or aquinazoline ring or atoms constituting a substituent are not included inthe number of ring atoms. When a fluorene ring is bonded with a fluorenering as a substituent (including a spirofluorene ring), for example, thenumber of atoms of the fluorene ring as a substituent is not included inthe number of ring atoms.

In the present specification, the “XX to YY carbon atoms” in the“substituted or unsubstituted ZZ group including XX to YY carbon atoms”means the number of carbon atoms when the ZZ group is unsubstituted. Thenumber of carbon atoms of a substituent when the group is substituted isnot included. Here, “YY” is larger than “XX”, and “XX” and “YY”independently mean an integer of 1 or more.

In the present specification, the “XX to YY atoms” in the “substitutedor unsubstituted ZZ group including XX to YY atoms” means the number ofatoms when the ZZ group is unsubstituted. The number of atoms of asubstituent when the group is substituted is not included. Here, “YY” islarger than “XX”, and “XX” and “YY” independently mean an integer of 1or more.

In the present specification, the “unsubstituted” in the “substituted orunsubstituted” means bonding of a hydrogen atom, not substitution by thesubstituent mentioned above.

As specific examples of each substituent in the present specification,the following can be given.

As the unsubstituted alkyl group including 1 to 50 (preferably 1 to 30,more preferably 1 to 18, and further preferably 1 to 5) carbon atoms, amethyl group, an ethyl group, a propyl group, an isopropyl group, ann-butyl group, a s-butyl group, an isobutyl group, a t-butyl group, ann-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group orthe like can be given, for example.

As the substituted alkyl group including 1 to 50 (preferably 1 to 30,more preferably 1 to 18, and further preferably 1 to 5) carbon atoms, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, a 1,2,3-trinitropropyl group, a1-pyrrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenyl-isopropyl groupor the like can be given.

The substituted or unsubstituted haloalkyl group including 1 to 50carbon atoms is a group in which one or more of hydrogen atoms of thealkyl group is substituted by a halogen atom. As the substituted orunsubstituted haloalkyl group including 1 to 50 carbon atoms, a groupobtained by substituting one or more halogen atoms in theabove-mentioned substituted or unsubstituted alkyl group including 1 to50 carbon atoms can be given.

As the unsubstituted alkenyl group including 2 to 50 (preferably 2 to30, more preferably 2 to 18) carbon atoms, a vinyl group, an allylgroup, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1,3-butanedienyl group, a 1-methylvinyl group, a 1-methylallyl group, a1,1-dimethylallyl group, a 2-methylally group, a 1,2-dimethylallyl groupor the like can be given.

As the unsubstituted alkynyl group including 2 to 50 (preferably 2 to30, more preferably 2 to 18) carbon atoms, an ethynyl group or the likecan be given.

As the unsubstituted cycloalkyl group including 3 to 50 (preferably 3 to30, more preferably 3 to 18, and further preferably 3 to 6) ring carbonatoms, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, acyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a2-adamantyl group, a 1-norbomyl group, a 2-norbomyl group or the likecan be given.

The unsubstituted alkoxy group including 1 to 50 (preferably 1 to 30,more preferably 1 to 18) carbon atoms is represented by —OX. As examplesof X, the alkyl group including 1 to 50 carbon atoms mentioned above canbe given, for example.

The unsubstituted alkyl group including 1 to 50 (preferably 1 to 30,more preferably 1 to 18) carbon atoms is represented by —SX. As examplesof X, the alkyl group including 1 to 50 carbon atoms mentioned above canbe given, for example.

As the unsubstituted aryl group including 6 to 50 (preferably 6 to 30,more preferably 6 to 18) ring carbon atoms, a phenyl group, a 1-naphthylgroup, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a9-anthryl group, a 9-phenanthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, am-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-ylgroup, a fluorenyl group or the like can be given.

Among these, a phenyl group, a naphthyl group, a biphenylyl group, aterphenyl group, a pyrenyl group, a phenanthryl group and a fluorenylgroup are preferable. A phenyl group, a naphthyl group, a biphenylylgroup, a terphenyl group, a pyrenyl group and a fluorenyl group are morepreferable.

As the substituted aryl group including 6 to 50 (preferably 6 to 30,more preferably 6 to 18) ring carbon atoms, an o-tolyl group, a m-tolylgroup, a p-tolyl group, a para-isopropylphenyl group, ameta-isopropylphenyl group, an ortho-isopropylphenyl group, ap-t-butylphenyl group, a meta-t-butylphenyl group, anortho-t-butylphenyl group, a 3,4,5-trimethylphenyl group, a4-phenoxyphenyl group, a 4-methoxyphenyl group, a 3,4-dimethoxyphenylgroup, a 3,4,5-trimethoxyphenyl group, a 4-(phenylsulfanyl) phenylgroup, a 4-(methylsulfanyl)phenyl group, a N′,N′-dimethyl-N-phenylgroup, a, 2,6-dimethylphenyl group, a 2-(phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a 9,9-dimethylfluorenyl group, a9,9-diphenylfluorenyl group, a 9,9′-spirobifluorenyl group, a9,9-di(4-methylphenyl)fluorenyl group, a9,9-di(4-isopropylphenyl)fluorenyl group, a9,9-di(4-t-butylphenyl)fluorenyl group, a chrysenyl group, afluoranthenyl group or the like can be given.

As the unsubstituted arylene group including 6 to 50 (preferably 6 to30, more preferably 6 to 18) ring carbon atoms, a divalent group formedof an aromatic hydrocarbon ring constituting the aryl group including 6to 50 ring carbon atoms exemplified above can be given.

The unsubstituted aryloxy group including 6 to 50 (preferably 6 to 30,more preferably 6 to 18) ring carbon atoms is represented by —OY Asexamples of Y, the aryl group including 6 to 50 ring carbon atomsmentioned above can be given.

The unsubstituted arylthio group including 6 to 50 (preferably 6 to 30,more preferably 6 to 18) ring carbon atoms is represented by —SY Asexamples of Y, the aryl group including 6 to 50 ring carbon atomsmentioned above can be given.

As the unsubstituted aralkyl group including 7 to 50 (preferably 7 to30, more preferably 7 to 18) carbon atoms, a benzyl group, a1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a2-phenylisopropyl group, a phenyl-t-butyl group, a α-naphthylmethylgroup, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group,1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group orthe like can be given.

As the substituted aralkyl group including 7 to 50 (preferably 7 to 30,more preferably 7 to 18) carbon atoms, a p-methylbenzyl group, am-methylbenzyl group, an o-methylbenzyl group, a p-chlorobenzyl group, am-chlorobenzyl group, an o-chlorobenzyl group, a p-bromobenzyl group, am-bromobenzyl group, an o-bromobenzyl group, a p-iodobenzyl group, am-iodobenzyl group, an o-iodobenzyl group, a p-hydroxybenzyl group, am-hydroxybenzyl group, an o-hydroxybenzyl group, a p-nitrobenzyl group,a m-nitrobenzyl group, an o-nitrobenzyl group, a p-cyanobenzyl group, am-cyanobenzyl group, an o-cyanobenzyl group or the like can be given,for example.

As the unsubstituted monovalent heterocyclic group including 5 to 50(preferably 5 to 30, more preferably 5 to 18) ring atoms, a pyrrolylgroup, a pyrazinyl group, a pyridinyl group, an indolyl group, anisoindolyl group, a furyl group, a benzofuranyl group, anisobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, and a thienyl group or the like, and a monovalentgroup formed of a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a triazine ring, an indole ring, a quinoline ring, anacridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, amorpholine ring, a piperazine ring, a carbazole ring, a furan ring, athiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring,a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazolering, an imidazole ring, a benzimidazole ring, a pyran ring, adibenzofuran ring, a benzo[a]dibenzofuran ring, a benzo[b]dibenzofuranring and benzo[c]dibenzofuran ring, a 1,3-benzodioxole ring, a2,3-dihydro-1,4-benzodioxine ring, a phenanthro[4,5-bcd] furan ring, abenzophenoxazine ring or the like can be given.

As the hetero atom constituting the heterocyclic group, in addition to ahetero atom such as S, O, N or the like, a hetero atom such as Si, Geand Se can be given.

As the unsubstituted divalent heterocyclic group including 5 to 50(preferably 5 to 30, more preferably 5 to 18) ring carbon atoms, adivalent group formed of the above-exemplified groups and the monovalentheterocyclic group or the like can be given.

As the substituted or unsubstituted monovalent heterocyclic groupincluding 5 to 50 ring atoms, the following groups are included. As thedivalent heterocyclic group including 5 to 50 ring atoms, groupsobtained by forming the following groups into divalent groups are alsoincluded.

-   -   wherein X_(1A) to X_(6A) and Y_(1A) to Y_(6A) are independently        an oxygen atom, a sulfur atom, a —NZ— group or a —NH-group. Z is        a substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms, a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms or a substituted        or unsubstituted alkyl group including 1 to 50 carbon atoms.        When two or more Zs are present, the two or more Zs may be the        same or different.

As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or the like can be given.

<Organic Electroluminescence Device>

The organic electroluminescence device according to one aspect of theinvention comprises a cathode, an anode and at least one organic layerdisposed between the cathode and the anode.

At least one layer of the at least one organic layer comprises thecompound represented by the following formulas (1-1) and (1-3), or thecompound represented by the following formulas (1-2) and (1-3):

-   -   wherein in the formulas (1-1), (1-2) and (1-3),    -   ring A is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms, a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms or a benzene ring represented by the following formula        (2);    -   two atomic bondings * in the formula (1-1) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   three atomic bondings * in the formula (1-2) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   one or more pairs of adjacent two or more of R₁ to R₁₆ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₁ to R₁₆ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄,        —COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro        group, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different;

-   -   wherein in the formula (2), at one of the two ring carbon atoms        indicated by * the atomic bonding extending from the benzene        ring B in the formula (1-1) or the formula (1-2) is bonded, and        at the other of the two ring carbon atoms indicated by *, the        atomic bonding extending from the benzene ring C in the formula        (1-3) is bonded;    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different; and    -   n is an integer of 1 or 2, and when n is 2, two R₁₇s may be the        same or different.

In the formulas (1-1), (1-2) and (1-3), the fused aryl ring is a ringobtained by fusion of plural aromatic rings. Therefore, biphenylobtained by bonding of two aromatic rings through a single bond is notincluded in the fused aryl ring.

In the formulas (1-1), (1-2) and (1-3), the fused heterocyclic ring is aring obtained by fusion of plural heterocyclic rings or a ring obtainedby fusion of a heterocyclic ring and an aromatic ring.

An explanation will be given on “one or more pairs of two or moreadjacent groups of R₁ to R₁₆ may form a substituted or unsubstituted,saturated or unsaturated ring”.

The “one or more pairs of two or more adjacent groups of R₁ to R₁₆” is acombination of R₁ and R₂, R₂ and R₃, R₃ and R₄, R₅ and R₆, R₆ and R₇, R₁and R₂ and R₃ or the like, for example.

For the substituent when the “substituted or unsubstituted” saturated orunsaturated ring is “substituted”, the same substituents as those for“substituted or unsubstituted” mentioned later can be given.

The “saturated or unsaturated ring” means, when R₁ and R₂ form a ring, aring formed by a carbon atom with which R₁ is bonded, a carbon atom withwhich R₂ is bonded and one or more arbitrary elements. Specifically,when a ring is formed by R₁ and R₂, if an unsaturated ring is formed bya carbon atom with which R₁ is bonded, a carbon atom with which R₂ isbonded and 4 carbon atoms, a ring formed by R₁ and R₂ is a benzene ring.

The “arbitrary element” is preferably a C element, a N element, an Oelement and a S element. In an arbitrary element (for example, in thecase of a C element or a N element), an atomic bonding that does notform a ring may be terminated with a hydrogen atom or the like.

The “one or more arbitrary elements” is preferably 2 or more and 15 orless, more preferably 3 or more and 12 or less, and further preferably 3or more and 5 or less arbitrary elements.

Hereinbelow, the “one or more pairs of two or more adjacent groups of Xto Y may form a substituted or unsubstituted, saturated or unsaturatedring” has the same meaning as the mentioned above, except that X ischanged to R₁ and Y is changed to R₁₆.

Hereinbelow, an explanation is made on a compound represented by theformulas (1-1) and (1-3), and a compound represented by the formulas(1-2) and (1-3).

The “*” in the formula (1-1) is an atomic bonding that is bonded withthe ring A in the formula (1-3). In the formula (1-1), there are two“*”s. The two “*”s are respectively bonded with a ring carbon atom inthe fused aryl ring in the ring A, a ring atom in the fused heterocyclicring, or a ring carbon atom of the benzene ring represented by theformula (2), and form a compound.

The “*” in the formula (1-2) is also an atomic bonding that is bondedwith the ring A in the formula (1-3). In the formula (1-2), there arethree “*”s. The three “*”s are respectively bonded with a ring carbonatom in the fused aryl ring in the ring A, a ring atom in the fusedheterocyclic ring, or a ring carbon atom of the benzene ring representedby the formula (2), and form a compound.

The “*” in the formula (2) indicates a bonding position. At one of thering carbon atoms indicated by the two *s, an atomic bonding extendingfrom the benzene ring B in the formula (1-1) or (1-2) is bonded, and atthe other of ring carbon atoms indicated by the two *s, an atomicbonding extending from the benzene ring C in the formula (1-3) isbonded.

In one embodiment, the compound represented by the formulas (1-1) and(1-3) or the compound represented by the formulas (1-2) and (1-3) arecompounds represented by the following formula (3), (4) or (5).

-   -   wherein in the formulas (3), (4) and (5),    -   the ring A′ is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms or a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms.    -   R₁ to R₇ and R₁₀ to R₁₇ are as defined in the formulas (1-1),        (1-2), (1-3) and (2).

In one embodiment, the substituted or unsubstituted fused aryl ringincluding 10 to 50 ring carbon atoms in the ring A in the formula (1-3)or the ring A in the formula (5) is a substituted or unsubstitutednaphthalene ring or a substituted or unsubstituted fluorene ring.

In one embodiment, the substituted or unsubstituted fused aryl ringincluding 10 to 50 ring carbon atoms in the ring A in the formula (1-3)or the ring A in the formula (5) may include, for example, 10 to 30, 10to 20 or 10 to 14 ring carbon atoms. As the fused aryl ring, asubstituted or unsubstituted naphthalene ring, a substituted orunsubstituted anthracene ring, or a substituted or unsubstitutedfluorene ring can be given.

In one embodiment, the substituted or unsubstituted fused heterocyclicring including 8 to 50 ring atoms in the ring A in the formula (1-3) orthe ring A in the formula (5) is a substituted or unsubstituteddibenzofurane ring, a substituted or unsubstituted carbazole ring or asubstituted or unsubstituted dibenzothiophene ring.

In one embodiment, the substituted or unsubstituted fused heterocyclicring including 8 to 50 ring atoms in the ring A in the formula (1-3) orthe ring A in the formula (5) is a substituted or unsubstituteddibenzofuran skeleton-containing structure (such as a substituted orunsubstituted dibenzofuran, a substituted or unsubstitutednaphthobenzofuran, a substituted or unsubstituted dinaphthofuran, andthe like), or a substituted or unsubstituted dibenzothiopheneskeleton-containing structure (such as a substituted or unsubstituteddibenzothiophene, a substituted or unsubstituted naphthobenzothiophene,a substituted or unsubstituted dinaphthothiophene, and the like).

In one embodiment, the substituted or unsubstituted fused heterocyclicring including 8 to 50 ring atoms in the ring A in the formula (1-3) orthe ring A in the formula (5) is a substituted or unsubstituteddibenzofuran ring or a substituted or unsubstituted dibenzothiophenering.

In one embodiment, the substituted or unsubstituted fused heterocyclicring including 8 to 50 ring atoms in the ring A in the formula (1-3) orthe ring A in the formula (5) is a substituted carbazoleskeleton-containing structure (such as a substituted carbazole ring),and the substituent is a substituted or unsubstituted aryl groupincluding 6 to 50 ring carbon atoms or a substituted or unsubstitutedmonovalent heterocyclic group including 5 to 50 ring atoms. The arylgroup or monovalent heterocyclic group of the above substituent is notbonded to the carbazole ring.

In one embodiment, the substituted or unsubstituted fused heterocyclicring including 8 to 50 ring atoms in the ring A in the formula (1-3) orthe ring A in the formula (5) is a substituted carbazoleskeleton-containing structure (such as a substituted carbazole ring),and the carbazole skeleton-containing structure has a substituent at9-position of the carbazole ring, and the substituent is a substitutedor unsubstituted aryl group including 6 to 50 ring carbon atoms or asubstituted or unsubstituted monovalent heterocyclic group including 5to 50 ring atoms. When the substituent is an unsubstituted phenyl group,the unsubstituted phenyl group is not bonded to the carbazoleskeleton-containing structure.

In one embodiment, in the compound represented by the formula (5), atleast one pair of R₅ and R₆, R₆ and R₇, R₁₄ and R₁₅, and R₁₅ and R₁₆forms a substituted or unsubstituted, saturated or unsaturated ring. Asthe ring structure to be formed, a substituted or unsubstituted fluorenering structure having ring B or ring C at one end, or a substituted orunsubstituted naphthalene ring structure having ring B or ring C at oneend can be given.

In one embodiment, in the compound represented by the formula (5), atleast one pair of R₁ and R₂, R₂ and R₃, R₃ and R₄, R₁₀ and R₁₁, R₁₁ andR₁₂, and R₁₂ and R₁₃ forms a substituted or unsubstituted, saturated orunsaturated ring. As the ring structure to be formed, a substituted orunsubstituted fluorene ring structure having a benzene ring, to which R₁to R₄ is bonded or a benzene ring to which R₁₀ to R₁₃ are bonded, at oneend, or a substituted or unsubstituted naphthalene ring structure havinga benzene ring, to which R₁ to R₄ is bonded or a benzene ring to whichR₁₀ to R₁₃ are bonded, at one end can be given.

In one embodiment, the compound represented by the formula (5) is acompound represented by any one of the following formulas (5-1) to(5-3):

-   -   wherein in the formulas (5-1) to (5-3),    -   ring A is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms or a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms;    -   R₁ to R₅, R₇, R₁₀ to R₁₄ and R₁₆ are as defined in the formulas        (1-1), (1-2), (1-3) and (2);    -   R₂₁ to R₂₆ and R₃₁ to R₃₆ are independently a hydrogen atom, a        substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃),        —C(═O)R₃₄,—COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group,        a nitro group, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   R₃₁ to R₃₇ are as defined in the formulas (1-1), (1-2), (1-3)        and (2).

In one embodiment, the compound represented by the formulas (1-1) and(1-3) or the compound represented by the formulas (1-2) and (1-3) areselected from the group consisting of compounds represented by thefollowing formulas (6-1) to (6-7):

-   -   wherein in the formulas (6-1) to (6-7),    -   R₁ to R₁₇ are as defined in the formulas (1-1), (1-2), (1-3) and        (2);    -   X is O, NR₂₅ or C(R₂₆) (R₂₇).    -   one or more pairs of adjacent two or more of R₂₁ to R₂₇ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₂₁ to R₂₇ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃),        —C(═O)R₃₄,—COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group,        a nitro group, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁ to R₃₇ may be the same or different.

In one embodiment, the compound represented by the formulas (1-1) and(1-3) or the compound represented by the formulas (1-2) and (1-3) areselected from the group consisting of compounds represented by thefollowing formulas (6-8) to (6-10):

-   -   wherein in the formulas (6-8) to (6-10),    -   R₁ to R₇ and R₁₀ to R₁₆ are as defined in the formulas (1-1),        (1-2), (1-3) and (2); one or more pairs of adjacent two or more        of R₂₁ to R₂₆ may form a substituted or unsubstituted, saturated        or unsaturated ring;    -   R₂₁ to R₂₆ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃,)(R₃₂)(R₃₃),        —C(═O)R₃₄,—COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group,        a nitro group, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁ to R₃₇ may be the same or different.

In one embodiment, the compound represented by the formulas (1-1) and(1-3) or the compound represented by the formulas (1-2) and (1-3) is acompound represented by the following formula (3-2):

-   -   wherein in the formula (3-2),    -   R₃, R₅, R₆, R₁₀, R₁₂ and R₁₃ are as defined in the formulas        (1-1) and (1-3).

In one embodiment, the compound represented by the formulas (1-1) and(1-3) or the compound represented by the formulas (1-2) and (1-3) is acompound represented by the following formula (7):

-   -   wherein in the formula (7),    -   R₃, R₅, R₆, R₁₂, R₁₄ and R₁₅ are as defined in the formula (1-2)        and the formula (1-3).

In one embodiment, R₁ to R₁₇ are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted aryl groupincluding 6 to 50 ring carbon atoms and a substituted or unsubstitutedheterocyclic group including 5 to 50 ring atoms.

In one embodiment, R₁ to R₁₇ are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted aryl groupincluding 6 to 18 ring carbon atoms and a substituted or unsubstitutedheterocyclic group including 5 to 18 ring atoms.

A substituent in the “substituted or unsubstituted” in the compoundrepresented by the formula (1-1) and (1-3) and the compound representedby the formula (1-2) and (1-3) is selected from the group consisting ofan alkyl group including 1 to 50 carbon atoms, a haloalkyl groupincluding 1 to 50 carbon atoms, an alkenyl group including 2 to 50carbon atoms, an alkynyl group including 2 to 50 carbon atoms, acycloalkyl group including 3 to 50 ring carbon atoms, an alkoxy groupincluding 1 to 50 carbon atoms, an alkylthio group including 1 to 50carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, anarylthio group including 6 to 50 ring carbon atoms, an aralkyl groupincluding 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄s,—S(═O)₂R₄₀, —P(═O)(R₄₇)(R₄₃), —Ge(R₄₉)(R₅₀)(R₅₁), —N(R₅₂)(R₅₃) (whereinR₄₁ to R₅₃ are independently a hydrogen atom, an alkyl group including 1to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms ora heterocyclic group including 5 to 50 ring atoms. When each of R₄₁s toR₅₃s are present in plural, each of the plural R₄₁s to R₅₃s may be thesame or different), a hydroxyl group, a halogen atom, a cyano group, anitro group, an aryl group including 6 to 50 ring carbon atoms, and amonovalent heterocyclic group including 5 to 50 ring atoms.

In one embodiment, the substituent in the “substituted or unsubstituted”in the compound represented by the formulas (1-1) and (1-3) and thecompound represented by the formulas (1-2) and (1-3) is an alkyl groupincluding 1 to 50 carbon atoms, an aryl group including 6 to 50 ringcarbon atoms and a monovalent heterocyclic group including 5 to 50 ringatoms.

In one embodiment, the substituent in the “substituted or unsubstituted”in the compound represented by the formulas (1-1) and (1-3) and thecompound represented by the formulas (1-2) and (1-3) is selected fromthe group consisting of an alkyl group including 1 to 18 carbon atoms,an aryl group including 6 to 18 ring carbon atoms and a monovalentheterocyclic group including 5 to 18 ring atoms.

Specific examples of each substituent, substituents for “substituted orunsubstituted” and halogen atoms in the compound represented by theformulas (1-1) and (1-3), and the compound represented by the formulas(1-2) and (1-3) are the same as those mentioned above.

As specific example of the compound represented by the formulas (1-1)and (1-3) and the compound represented by the formulas (1-2) and (1-3),the following compounds can be given, for example.

The compound represented by the formulas (1-1) and (1-3) and thecompound represented by the formulas (1-2) and (1-3) can be synthesizedin accordance with the reaction conducted in the Examples, and by usinga known alternative reaction or raw materials suited to an intendedproduct, for example.

In another aspect of the invention, an organic electroluminescencedevice has a cathode, an anode, and at least one organic layer disposedbetween the cathode and the anode.

The at least one layer of the at least one organic layer comprises acompound represented by the following formula (3-11):

-   -   wherein in the formula (3-11),    -   one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ to        R₁₆ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁ to R₇ and R₁₀ to R₁₆ that do not form the substituted or        unsubstituted, saturated or unsaturated ring are independently a        hydrogen atom, a substituted or unsubstituted alkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        haloalkyl group including 1 to 50 carbon atoms, a substituted or        unsubstituted alkenyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted alkynyl group including 2 to 50        carbon atoms, a substituted or unsubstituted cycloalkyl group        including 3 to 50 ring carbon atoms, a substituted or        unsubstituted alkoxy group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkylthio group including 1 to 50        carbon atoms, a substituted or unsubstituted aryloxy group        including 6 to 50 ring carbon atoms, a substituted or        unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃,)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms, provided that        at least one of R₁ to R₇ and R₁₀ to R₁₆ is —N(R₃₆)(R₃₇);    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   two R₁₇s may be the same or different;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different.

An explanation will be given on the feature that “one or more pairs oftwo or more adjacent groups of R₁ to R₇ and R₁₀ to R₁₆ may form asubstituted or unsubstituted, saturated or unsaturated ring.”

The “one or more pairs of two or more adjacent groups of R₁ to R₇ andR₁₀ to R₁₆” is a combination of: for example, R₁ and R₂; R₂ and R₃; R₃and R₄; R₅ and R₆; R₆ and R₇; R₁ and R₂ and R₃ or the like.

For the substituent when the “substituted or unsubstituted” saturated orunsaturated ring is “substituted”, the same substituents as those for“substituted or unsubstituted” mentioned later can be given.

The “saturated or unsaturated ring” means, as an example when R₁ and R₂form a ring, a ring formed by: a carbon atom with which R₁ is bonded; acarbon atom with which R₂ is bonded; and one or more arbitrary elements.Specifically, when a ring is formed by R₁ and R₂, if an unsaturated ringis formed by a carbon atom with which R₁ is bonded, a carbon atom withwhich R₂ is bonded and 4 carbon atoms, a ring formed by R₁ and R₂ is abenzene ring.

The “arbitrary element” is preferably a C element, a N element, an Oelement and a S element. For an arbitrary element (for example, in thecase of a C element or a N element), an atomic bonding that does notform a ring may be terminated with a hydrogen atom or the like.

The “one or more arbitrary elements” are preferably 2 or more and 15 orless, more preferably 3 or more and 12 or less, and further preferably 3or more and 5 or less arbitrary elements.

Hereinbelow, the expression “one or more pairs of two or more adjacentgroups of X to Y may form a substituted or unsubstituted, saturated orunsaturated ring” has the same meaning as the mentioned above, exceptthat X is changed to R₁ and Y is changed to R₁₆.

In one embodiment, the compound represented by the formula (3-11) is acompound represented by the following formula (3-12):

-   -   wherein in the formula (3-12),    -   R₁ to R₇ and R₁₀ to R₁₆ are as defined in the formula (3-11),        provided that any two of R₁ to R₇ and R₁₀ to R₁₆ are        —N(R₃₆)(R₃₇).

In one embodiment, R₁ to R₇ and R₁₀ to R₁₆ are independently selectedfrom the group consisting of a hydrogen atom, a substituted orunsubstituted aryl group including 6 to 50 ring carbon atoms and asubstituted or unsubstituted heterocyclic group including 5 to 50 ringatoms.

In one embodiment, R₁ to R₇ and R₁₀ to R₁₆ are independently selectedfrom the group consisting of a hydrogen atom, a substituted orunsubstituted aryl group including 6 to 18 ring carbon atoms and asubstituted or unsubstituted heterocyclic group including 5 to 18 ringatoms.

A substituent in the “substituted or unsubstituted” in the compoundrepresented by the formula (3-11) is selected from the group consistingof an alkyl group including 1 to 50 carbon atoms, a haloalkyl groupincluding 1 to 50 carbon atoms, an alkenyl group including 2 to 50carbon atoms, an alkynyl group including 2 to 50 carbon atoms, acycloalkyl group including 3 to 50 ring carbon atoms, an alkoxy groupincluding 1 to 50 carbon atoms, an alkylthio group including 1 to 50carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, anarylthio group including 6 to 50 ring carbon atoms, an aralkyl groupincluding 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄₅,—S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₈), —Ge(R₄₉)(R₅₀)(R₅₁), —N(R₅₂)(R₅₃) (R₄₁ toR₅₃ are independently a hydrogen atom, an alkyl group including 1 to 50carbon atoms, an aryl group including 6 to 50 ring carbon atoms or aheterocyclic group including 5 to 50 ring atoms. When each of R₄₁ to R₅₃is present in plural, each of the plural R₄₁s to R₅₃s may be the same ordifferent.), a hydroxyl group, a halogen atom, a cyano group, a nitrogroup, an aryl group including 6 to 50 ring carbon atoms, and amonovalent heterocyclic group including 5 to 50 ring atoms.

In one embodiment, the substituent in the “substituted or unsubstituted”in the compound represented by the formula (3-11) is an alkyl groupincluding 1 to 50 carbon atoms, an aryl group including 6 to 50 ringcarbon atoms and a monovalent heterocyclic group including 5 to 50 ringatoms.

In one embodiment, the substituent in the “substituted or unsubstituted”in the compound represented by the formula (3-11) is selected from thegroup consisting of an alkyl group including 1 to 18 carbon atoms, anaryl group including 6 to 18 ring carbon atoms and a monovalentheterocyclic group including 5 to 18 ring atoms.

Specific examples of each substituent, substituents for “substituted orunsubstituted” and halogen atoms in the compound represented by theformula (3-11) are the same as those mentioned above.

In one embodiment, the compound represented by the formula (3-11) is acompound represented by the following formula (3-13):

-   -   wherein in the formula (3-13),    -   one or more pairs of adjacent two or more of R₁ to R₄ and R₁₀ to        R₁₃ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁ to R₄, R₁₀ to R₁₃, and R₁₇ that do not form the substituted        or unsubstituted, saturated or unsaturated ring are        independently a hydrogen atom, a substituted or unsubstituted        aryl group including 6 to 18 ring carbon atoms or a substituted        or unsubstituted monovalent heterocyclic group including 6 to 18        ring atoms;    -   two R₁₇s may be the same or different; and    -   R_(A), R_(B), R_(C) and R_(D) are independently a substituted or        unsubstituted aryl group including 6 to 18 ring carbon atoms or        a substituted or unsubstituted monovalent heterocyclic group        including 6 to 18 ring atoms.

An explanation will be given on the feature that “one or more pairs oftwo or more adjacent groups of R₁ to R₄ and R₁₀ to R₁₃ may form asubstituted or unsubstituted, saturated or unsaturated ring.”

The “one or more pairs of two or more adjacent groups of R₁ to R₄ andR₁₀ to R₁₃” is a combination of: for example, R₁ and R₂; R₂ and R₃; R₃and R₄; R₁ and R₂ and R₃ or the like.

For the substituent when the “substituted or unsubstituted” saturated orunsaturated ring is “substituted”, the same substituents as those for“substituted or unsubstituted” mentioned later can be given.

The “saturated or unsaturated ring” means the same as explained in theabove formula (3-11).

In the compound represented by the formula (3-13), one or more pairs ofadjacent two or more of R₁ to R₄, R₁₀ to R₁₃ and R₁₇ may form asubstituted or unsubstituted, saturated or unsaturated ring and may notform a substituted or unsubstituted, saturated or unsaturated ring. Inthe compound represented by formula (3-13), it is preferable that one ormore pairs of adjacent two or more of R₁ to R₄, R₁₀ to R₁₃ and R₁₇ donot form a substituted or unsubstituted, saturated or unsaturated ring.

In one embodiment, the compound represented by the formula (3-13) is acompound represented by the following formula (3-14):

-   -   wherein in the formula (3-14),    -   R₁₇, R_(A), R_(B), R_(C) and R_(D) are as defined in the formula        (3-13).

In one embodiment, R_(A), R_(B), R_(C) and R_(D) of the compoundrepresented by formula (3-13) and the compound represented by formula(3-14) are independently a substituted or unsubstituted aryl groupincluding 6 to 18 ring carbon atoms.

In one embodiment, R_(A), R_(B), R_(C) and R_(D) of the compoundrepresented by formula (3-13) and the compound represented by formula(3-14) are independently a substituted or unsubstituted phenyl group.

In one embodiment, two R₁₇s of the compound represented by formula(3-13) and the compound represented by formula (3-14) are independentlya hydrogen atom.

A substituent in the “substituted or unsubstituted” in the compoundrepresented by the formula (3-13) and the compound represented by theformula (3-14) is selected from the group consisting of an alkyl groupincluding 1 to 18 carbon atoms, an aryl group including 6 to 18 ringcarbon atoms, and a monovalent heterocyclic group including 5 to 18 ringatoms.

In one embodiment, a substituent in the “substituted or unsubstituted”in the compound represented by the formula (3-13) and the compoundrepresented by the formula (3-14) is an alkyl group including 1 to 5carbon atoms.

Specific examples of each substituent and substituents for “substitutedor unsubstituted” in the compound represented by the formulas (3-13) and(3-14) are the same as those mentioned above.

In another aspect of the invention, an organic electroluminescencedevice has a cathode, an anode, and at least one organic layer disposedbetween the cathode and the anode.

The at least one layer of the at least one organic layer comprises acompound represented by the following formula (3-21):

-   -   wherein in the formula (3-21),    -   one or more pairs of adjacent two or more of R₁ to R₄ and R₁₀ to        R₁₃ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁ to R₄, R₁₀ to R₁₃, and R₁₇ that do not form the substituted        or unsubstituted, saturated or unsaturated ring are        independently a hydrogen atom, a substituted or unsubstituted        aryl group including 6 to 20 ring carbon atoms or a substituted        or unsubstituted monovalent heterocyclic group including 5 to 20        ring atoms;    -   two R₁₇s may be the same or different; and R_(A), R_(B), R_(C)        and R_(D) are independently a substituted or unsubstituted aryl        group including 6 to 20 ring carbon atoms.

The “one or more pairs of adjacent two or more of R₁ to R₄ and R₁₀ toR₁₃ may form a substituted or unsubstituted, saturated or unsaturatedring” means the same as explained in the above formula (3-13).

For the substituent when the “substituted or unsubstituted” saturated orunsaturated ring is “substituted”, the same substituents as those for“substituted or unsubstituted” mentioned later can be given.

The “saturated or unsaturated ring” means the same as explained in theabove formula (3-11).

In the compound represented by the formula (3-21), one or more pairs ofadjacent two or more of R₁ to R₄, R₁₀ to R₁₃ and R₁₇ may form asubstituted or unsubstituted, saturated or unsaturated ring and may notform a substituted or unsubstituted, saturated or unsaturated ring. Inthe compound represented by formula (3-21), it is preferable that one ormore pairs of adjacent two or more of R₁ to R₄, R₁₀ to R₁₃ and R₁₇ donot form a substituted or unsubstituted, saturated or unsaturated ring.

In one embodiment, the compound represented by the formula (3-21) is acompound represented by the following formula (3-22):

-   -   wherein in the formula (3-22), R₁₇, R_(A), R_(B), R_(C) and        R_(D) are as defined in the formula (3-21).

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), R_(A), R_(B), R_(C) and R_(D) are independently asubstituted or unsubstituted phenyl group.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), two R₁₇s are independently a hydrogen atom.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), a substituent in the “substituted or unsubstituted” isselected from the group consisting of an alkyl group including 1 to 20carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and amonovalent heterocyclic group including 5 to 20 ring atoms.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), a substituent in the “substituted or unsubstituted” is analkyl group including 1 to 5 carbon atoms.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), R_(A), R_(B), R_(C) and R_(D) are independently asubstituted or unsubstituted phenyl group; and two R₁₇s areindependently a hydrogen atom.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), R_(A), R_(B), R_(C) and R_(D) are independently asubstituted or unsubstituted phenyl group; two R₁₇s are independently ahydrogen atom; and a substituent in the “substituted or unsubstituted”is selected from the group consisting of an alkyl group including 1 to20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, anda monovalent heterocyclic group including 5 to 20 ring atoms.

In one embodiment, in the compound represented by the formulas (3-21)and (3-22), R_(A), R_(B), R_(C) and R_(D) are independently asubstituted or unsubstituted phenyl group; two R₁₇s are independently ahydrogen atom; and a substituent in the “substituted or unsubstituted”is an alkyl group including 1 to 5 carbon atoms.

In another aspect of the invention, an organic electroluminescencedevice has a cathode, an anode, and at least one organic layer disposedbetween the cathode and the anode.

The at least one layer of the at least one organic layer comprises acompound represented by the following formulas (3-31) or (3-32):

-   -   wherein in the formulas (3-31) and (3-32),    -   one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ to        R₁₆ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁₇, and R₁ to R₇ and R₁₀ to R₁₆ that do not form the        substituted or unsubstituted, saturated or unsaturated ring are        independently a hydrogen atom, a substituted or unsubstituted        aryl group including 6 to 20 ring carbon atoms or a substituted        or unsubstituted monovalent heterocyclic group including 5 to 20        ring atoms;    -   two R₁₇S may be the same or different; and    -   Ar₁ to Ar₄ are independently a substituted or unsubstituted aryl        group including 6 to 20 ring carbon atoms.

An explanation will be given on the feature that “one or more pairs oftwo or more adjacent groups of R₁ to R₇ and R₁₀ to R₁₆ may form asubstituted or unsubstituted, saturated or unsaturated ring.”

The “one or more pairs of to or more adjacent groups of R₁ to R₇ and R₁₀to R₁₆” is a combination of: for example, R₃ and R₄; R₅ and R₆; R₆ andR₇; R₅ and R₆ and R₇ or the like in the formula (3-31), and R₁ and R₂;R₂ and R₃; R₅ and R₆; R₆ and R₇; R₁ and R₂ and R₃ or the like in theformula (3-32).

For the substituent when the “substituted or unsubstituted” saturated orunsaturated ring is “substituted”, the same substituents as those for“substituted or unsubstituted” mentioned later can be given.

The “saturated or unsaturated ring” means the same as explained in theabove formula (3-11).

In the formulas (3-31) and (3-32), one or more pairs of adjacent two ormore of R₁ to R₇ and R₁₀ to R₁₆ may not form a substituted orunsubstituted, saturated or unsaturated ring;

In one embodiment, the compound represented by the following formula(3-31) or (3-32) is a compound represented by the following formula(3-33) or (3-34):

-   -   wherein in the formulas (3-33) and (3-34),    -   R₅ to R₇, R₁₄ to R₁₇ and Ar₁ to Ar₄ are as defined in the        formulas (3-31) and (3-32).

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), Ar₁ to Ar₄ are independently a substituted or unsubstitutedphenyl group.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), two R₁₇s are independently a substituted or unsubstituted arylgroup including 6 to 20 ring carbon atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), two R₁₇s are independently a substituted or unsubstituted phenylgroup.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), two R₁₇s are hydrogen atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), a substituent in the “substituted or unsubstituted” is selectedfrom the group consisting of an alkyl group including 1 to 20 carbonatoms, an aryl group including 6 to 20 ring carbon atoms, and amonovalent heterocyclic group including 5 to 20 ring atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), a substituent in the “substituted or unsubstituted” is an alkylgroup including 1 to 5 carbon atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), Ar₁ to Ar₄ are independently a substituted or unsubstitutedphenyl group; and two R₁₇s are hydrogen atoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), Ar₁ to Ar₄ are independently a substituted or unsubstitutedphenyl group; two R₁₇s are independently a substituted or unsubstitutedaryl group including 6 to 20 ring carbon atoms; R₅ to R₇ and R₁₄ to R₁₆are hydrogen atoms; and a substituent in the “substituted orunsubstituted” is selected from the group consisting of an alkyl groupincluding 1 to 20 carbon atoms, an aryl group including 6 to 20 ringcarbon atoms, and a monovalent heterocyclic group including 5 to 20 ringatoms.

In one embodiment, in the compound represented by the formulas (3-31) to(3-34), Ar₁ to Ar₄ are independently a substituted or unsubstitutedphenyl group; two R₁₇s are independently a substituted or unsubstitutedphenyl group; R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms; and asubstituent in the “substituted or unsubstituted” is an alkyl groupincluding 1 to 5 carbon atoms.

Specific examples of each substituent and substituents for “substitutedor unsubstituted” in the compound represented by the formulas (3-31) to(3-34) are the same as those mentioned above.

As a specific example of the compound represented by the formulas (3-11)to (3-14), (3-21), (3-22) and (3-31) to (3-34), the following compoundscan be given, for example.

In the present specification, regarding “at least one organic layerdisposed between the cathode and the anode”, if only one organic layeris present between the cathode and the anode, it means the layer, and ifplural organic layers are present between the cathode and the anode, itmeans at least one layer thereof.

Further, regarding “the at least one organic layer comprises an emittinglayer”, if only one organic layer is present between the cathode and theanode, it means that the layer is an emitting layer, and if pluralorganic layers are present, it means that at least one of these layersis an emitting layer.

In one embodiment, the organic EL device has a hole-transporting layerbetween the anode and the emitting layer.

In one embodiment, the organic EL device has an electron-transportinglayer between the cathode and the emitting layer.

In the present specification, regarding the “at least one layer betweenthe emitting layer and the anode”, if only one organic layer is presentbetween the emitting layer and the anode, it means that layer, and ifplural organic layers are present, it means at least one layer thereof.For example, if two or more organic layers are present between theemitting layer and the anode, an organic layer nearer to the emittinglayer is called the “hole-transporting layer”, and an organic layernearer to the anode is called the “hole-injecting layer”. Each of the“hole-transporting layer” and the “hole-injecting layer” may be a singlelayer or may be formed of two or more layers. One of these layers may bea single layer and the other may be formed of two or more layers.

Similarly, regarding the “at least one layer between the emitting layerand the cathode”, if only one organic layer is present between theemitting layer and the cathode, it means that layer, and if pluralorganic layers are present, it means at least one layer thereof. Forexample, if two or more organic layers are present between the emittinglayer and the cathode, an organic layer nearer to the emitting layer iscalled the “electron-transporting layer”, and an organic layer nearer tothe cathode is called the “electron-injecting layer”. Each of the“electron-transporting layer” and the “electron-injecting layer” may bea single layer or may be formed of two or more layers. One of theselayers may be a single layer and the other may be formed of two or morelayers.

In one embodiment, the “at least one organic layer” mentioned abovecomprises the emitting layer, the emitting layer comprises a compoundrepresented by the formulas (1-1) and (1-3) or a compound represented bythe formulas (1-2) and (1-3). The compound represented by the formulas(1-1) and (1-3) or a compound represented by the formulas (1-2) and(1-3) can function as a fluorescent emitting material and can enhancethe luminous efficiency of the organic EL device.

In one embodiment, the “at least one organic layer” mentioned abovecomprises the emitting layer, and the emitting layer comprises acompound represented by the formula (3-11). The compound represented bythe formula (3-11) can function as a fluorescent emitting material andcan enhance the luminous efficiency of the organic EL device.

In one embodiment, the “at least one organic layer” mentioned abovecomprises the emitting layer, the emitting layer comprises a compoundrepresented by the formula (3-21). The compound represented by theformula (3-21) can function as a fluorescent emitting material and canenhance the luminous efficiency of the organic EL device.

In one embodiment, the “at least one organic layer” mentioned abovecomprises the emitting layer, the emitting layer comprises a compoundrepresented by the formula (3-31) or (3-32). The compound represented bythe formula (3-31) or (3-32) can function as a fluorescent emittingmaterial and can enhance the luminous efficiency of the organic ELdevice.

In one embodiment, the “at least one organic layer” mentioned abovecomprises a compound represented by the formulas (1-1) and (1-3) or acompound represented by the formulas (1-2) and (1-3). The compoundrepresented by the formulas (1-1) and (1-3) or the compound representedby the formulas (1-2) and (1-3) can function as a fluorescent emittingmaterial and can enhance the luminous efficiency of the organic ELdevice.

In one embodiment, the “at least one organic layer” mentioned abovecomprises a compound represented by formula (3-11). The compoundrepresented by the formula (3-11) is comprised as an emitting materialand can enhance the luminous efficiency of the organic EL device.

In one embodiment, the “at least one organic layer” mentioned abovecomprises a compound represented by formula (3-21). The compoundrepresented by the formula (3-21) is comprised as an emitting materialand can enhance the luminous efficiency of the organic EL device.

In one embodiment, the “at least one organic layer” mentioned abovecomprises a compound represented by formula (3-31) or (3-32). Thecompound represented by the formula (3-31) or (3-32) is comprised as anemitting material and can enhance the luminous efficiency of the organicEL device.

In one embodiment, the emitting layer further comprises a compoundrepresented by the following formula (10) (hereinafter may be referredto as the compound (10)):

-   -   wherein the formula (10),    -   one or more pairs of two or more adjacent R₁₀₁ to R₁₁₀ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₁₀₁ to R₁₁₀ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylene group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₁₂₁)(R₁₂₂)(R₁₂₃),        —C(═O)R₁₂₄, —COOR₁₂₅, —N(R₁₂₆)(R₁₂₇), a halogen atom, a cyano        group, a nitro group, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms, a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms, or a group represented by the following formula        (31);    -   R₁₂₁ to R₁₂₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; when each of R₁₂₁ to R₁₂₇ is present in plural, each        of the plural R₁₂₁ to R₁₂₇ may be the same or different;    -   provided that at least one of R₁₀₁ to R₁₁₀ that do not form the        substituted or unsubstituted, saturated or unsaturated ring is a        group represented by the following formula (31). If two or more        groups represented by the formula (31) are present, each of        these groups may be the same or different;

-L₁₀₁-Ar₁₀₁  (31)

-   -   wherein in the formula (31),    -   L₁₀₁ is a single bond, a substituted or unsubstituted arylene        group including 6 to 30 ring carbon atoms or a substituted or        unsubstituted divalent heterocyclic group including 5 to 30 ring        atoms;    -   Ar₁₀₁ is a substituted or unsubstituted aryl group including 6        to 50 ring carbon atoms or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms.

Specific examples of each substituent, substituents for “substituted orunsubstituted” and the halogen atom in the compound (10) are the same asthose mentioned above.

An explanation will be given on “one or more pairs of two or moreadjacent R₁₀₁ to R₁₁₀ may form a substituted or unsubstituted, saturatedor unsaturated ring”.

The “one pair of two or more adjacent R₁₀₁ to R₁₁₀” is a combination ofR₁₀₁ and R₁₀₂, R₁₀₂ and R₁₀₃, R₁₀₃ and R₁₀₄, R₁₀₅ and R₁₀₆, R₁₀₆ andR₁₀₇, R₁₀₇ and R₁₀₈, R₁₀₈ and R₁₀, R₁₀₁ and R₁₀₂ and R₁₀₃ or the like,for example.

The substituent in “substituted” in the “substituted or unsubstituted”for the saturated or unsaturated ring is the same as those for“substituted or unsubstituted” mentioned in the formula (10).

The “saturated or unsaturated ring” means, when R₁₀₁ and R₁₀₂ form aring, for example, a ring formed by a carbon atom with which R₁₀₁ isbonded, a carbon atom with which R₁₀₂ is bonded and one or morearbitrary elements. Specifically, when a ring is formed by R₁₀₁ andR₁₀₂, when an unsaturated ring is formed by a carbon atom with whichR₁₀₁ is bonded, a carbon atom with R₁₀₂ is bonded and four carbon atoms,the ring formed by R₁₀₁ and R₁₀₂ is a benzene ring.

The “arbitrary element” is preferably a C element, a N element, an Oelement and a S element. In the arbitrary element (C element or Nelement, for example), atomic bondings that do not form a ring may beterminated by a hydrogen atom, or the like.

The “one or more arbitrary element” is preferably 2 or more and 15 orless, more preferably 3 or more and 12 or less, and further preferably 3or more and 5 or less arbitrary elements.

For example, R₁₀₁ and R₁₀₂ may form a ring, and simultaneously, R₁₀₅ andR₁₀₆ may form a ring. In this case, the compound represented by theformula (10) is a compound represented by the following formula (10A),for example:

In one embodiment, R₁₀₁ to R₁₁₀ are independently a hydrogen atom, asubstituted or unsubstituted alkyl group including 1 to 50 carbon atoms,a substituted or unsubstituted aryl group including 6 to 50 ring carbonatoms, a substituted or unsubstituted heterocyclic group including 5 to50 ring atoms or a group represented by the formula (31).

In one embodiment, R₁₀₁ to R₁₁₀ are independently a hydrogen atom, asubstituted or unsubstituted aryl group including 6 to 50 ring carbonatoms, a substituted or unsubstituted heterocyclic group including 5 to50 ring atoms or a group represented by the formula (31).

In one embodiment, R₁₀₁ to R₁₁₀ are independently a hydrogen atom, asubstituted or unsubstituted aryl group including 6 to 18 ring carbonatoms, a substituted or unsubstituted heterocyclic group including 5 to18 ring atoms or a group represented by the formula (31).

In one embodiment, at least one of R₁₀₉ and R₁₁₀ is a group representedby the formula (31).

In one embodiment, R₁₀₉ and R₁₁₀ are independently a group representedby the formula (31).

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-1):

wherein in the formula (10-1), R₁₀₁ to R₁₀₈, L₁₀₁ and Ar₁₀₁ are asdefined in the formula (10).

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-2):

wherein in the formula (10-2), R₁₀₁, R₁₀₃ to R₁₀₈, L₁₀₁ and Ar₁₀₁ are asdefined in the formula (10).

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-3):

-   -   wherein in the formula (10-3),    -   R_(101A) to R_(108A) are independently a hydrogen atom or a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms;    -   L_(101A) is a single bond or a substituted or unsubstituted        arylene group including 6 to 30 ring carbon atoms, and the two        L_(101A)s may be the same or different;    -   Ar_(101A) is a substituted or unsubstituted aryl group including        6 to 50 ring carbon atoms, and the two Ar_(101A)s may be the        same or different.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-4):

-   -   wherein in the formula (10-4),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are independently a hydrogen atom or a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms;    -   X₁₁ is O, S, or N(R₆₁);    -   R₆₁ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms or a substituted or        unsubstituted aryl group including 6 to 50 ring carbon atoms;    -   one of R₆₂ to R₆₉ is an atomic bonding that is bonded with L₁₀₁;    -   one or more pairs of adjacent R₆₂ to R₆₉ that are not bonded        with L₁₀₁ may be bonded with each other to form a substituted or        unsubstituted, saturated or unsaturated ring; and    -   R₆₂ to R₆₉ that are not bonded with L₁₀₁ and do not form the        substituted or unsubstituted, saturated or unsaturated ring are        independently a hydrogen atom, a substituted or unsubstituted        alkyl group including 1 to 50 carbon atoms or a substituted or        unsubstituted aryl group including 6 to 50 ring carbon atoms.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-4A):

-   -   wherein in the formula (10-4A),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are independently a hydrogen atom or a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms;    -   X₁₁ is O, S or N(R₆₁);    -   R₆₁ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms or a substituted or        unsubstituted aryl group including 6 to 50 ring carbon atoms;        one or more pairs of adjacent two or more of R_(62A) to R_(69A)        may form a substituted or unsubstituted, saturated or        unsaturated ring, and adjacent two of R_(62A) to R_(69A) form a        ring represented by the following formula (10-4A-1); and    -   R_(62A) to R_(69A) that do not form a substituted or        unsubstituted, saturated or unsaturated ring are independently a        hydrogen atom, a substituted or unsubstituted alkyl group        including 1 to 50 carbon atoms or a substituted or unsubstituted        aryl group including 6 to 50 ring carbon atoms.

-   -   wherein in the formula (10-4A-1),    -   each of the two atomic bondings * is bonded with adjacent two of        R_(62A) to R_(69A);    -   one of R₇₀ to R₇₃ is an atomic bonding that is bonded with L₁₀₁;        and    -   R₇₀ to R₇₃ that are not bonded with L₁₀₁ are independently a        hydrogen atom, a substituted or unsubstituted alkyl group        including 1 to 50 carbon atoms or a substituted or unsubstituted        aryl group including 6 to 50 ring carbon atoms.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-6):

-   -   wherein in the formula (10-6),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are as defined in the formula (10-4);    -   R₆₆ to R₆₉ are as defined in the formula (10-4); and    -   X₁₂ is O or S.

In one embodiment, the compound represented by the formula (10-6) is acompound represented by the following formula (10-6H):

-   -   wherein in the formula (10-6H),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R₆₆ to R₆₉ are as defined in the formula (10-4); and    -   X₁₂ is O or S.

In one embodiment, the compound represented by the formulas (10-6) and(10-6H) is a compound represented by the following formula (10-6Ha):

-   -   wherein in the formula (10-6Ha),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10); and    -   X₁₂ is O or S.

In one embodiment, the compound represented by the formulas (10-6),(10-6H) and (10-6Ha) is a compound represented by the following formula(10-6Ha-1) or (10-6Ha-2):

-   -   wherein in the formula (10-6Ha-1) and (10-6Ha-2),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10); and    -   X₁₂ is O or S.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-7):

-   -   wherein in the formula (10-7),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are as defined in the formula (10-4);    -   X₁₁ is as defined in the formula (10-4); and    -   R₆₂ to R₆₉ are as defined in the formula (10-4), provided that        any one pair of R₆₆ and R₆₇, R₆₇ and R₆₈, and R₆₈ and R₆₉ are        bonded with each other to form a substituted or unsubstituted,        saturated or unsaturated ring.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-7H):

-   -   wherein in the formula (10-7H),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   X₁₁ is as defined in the formula (10-4); and    -   R₆₂ to R₆₉ are as defined in the formula (10-4), provided that        any one pair of R₆₆ and R₆₇, R₆₇ and R₆₈, and R₆₈ and R₆₉ are        bonded with each other to form a substituted or unsubstituted,        saturated or unsaturated ring.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-8):

-   -   wherein in the formula (10-8),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are as defined in the formula (10-4);    -   X₁₂ is O or S; and    -   R₆₆ to R₆₉ are as defined in the formula (10-4), provided that        any one pair of R₆₆ and R₆₇, R₆₇ and R₆₈, as well as R₆₈ and R₆₉        are bonded with each other to form a substituted or        unsubstituted, saturated or unsaturated ring.

In one embodiment, the compound represented by the formula (10-8) is acompound represented by the following formula (10-8H):

In the formula (10-8H), L₁₀₁ and Ar₁₀₁ are as defined in the formula(10).

R₆₆ to R₆₉ are as defined in the formula (10-4), provided that any onepair of R₆₆ and R₆₇, R₆₇ and R₆₈, as well as R₆₈ and R₆₉ are bonded witheach other to form a substituted or unsubstituted, saturated orunsaturated ring. Any one pair of R₆₆ and R₆₇, R₆₇ and Rea, as well asR₆₈ and R₆₉ may preferably be bonded with each other to form anunsubstituted benzene ring; and

-   -   X₁₂ is O or S.

In one embodiment, as for the compound represented by the formula(10-7), (10-8) or (10-8H), any one pair of R₆₆ and R₆₇, R₆₇ and Rea, aswell as R₆₈ and R₆₉ are bonded with each other to form a ringrepresented by the following formula (10-8-1) or (10-8-2), and R₆₆ toR₆₉ that do not form the ring represented by the formula (10-8-1) or(10-8-2) do not form a substituted or unsubstituted, saturated orunsaturated ring.

-   -   wherein in the formulas (10-8-1) and (10-8-2),    -   the two atomic bondings * are independently bonded with one pair        of R₆₆ and R₆₇, R₆₇ and R₆₈, or R₆₈ and R₆₉;    -   R₈₀ to R₈₃ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms or a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms; and    -   X₁₃ is O or S.

In one embodiment, the compound (10) is a compound represented by thefollowing formula (10-9):

-   -   wherein in the formula (10-9),    -   L₁₀₁ and Ar₁₀₁ are as defined in the formula (10);    -   R_(101A) to R_(108A) are as defined in the formula (10-4);    -   R₆₆ to R₆₉ are as defined in the formula (10-4), provided that        R₆₆ and R₆₇, R₆₇ and R₆₈, as well as R₆₈ and R₆₉ are not bonded        with each other and do not form a substituted or unsubstituted,        saturated or unsaturated ring; and    -   X₁₂ is O or S.

In one embodiment, the compound (10) is selected from the groupconsisting of compounds represented by the following formulas (10-10-1)to (10-10-4).

In the formulas (10-10-1) to (10-10-4), L_(101A), Ar_(101A) and R_(101A)to R_(108A) are as defined in the formula (10-3).

In one embodiment, the compound represented by the above formulas(10-10-1) to (10-10-4) is a compound represented by the followingformulas (10-10-1H) to (10-10-4H):

In the formulas (10-10-1H) to (10-10-4H), L_(101A) and Ar_(101A) are asdefined in the formula (10-3).

As for the compound represented by the formula (10), the followingcompounds can be given as specific examples.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formulas (1-1) and (1-3) or the compound representedby the formulas (1-2) and (1-3) and the compound represented by theformula (10), the content of the compound represented by the formulas(1-1) and (1-3) or the compound represented by the following formulas(1-2) and (1-3) is preferably 1 mass % or more and 20 mass % or lessrelative to the entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formulas (1-1) and (1-3) or the compound representedby the formulas (1-2) and (1-3) and the compound represented by theformula (10), the content of the compound represented by the formula(10) is preferably 80 mass % or more and 99 mass % or less relative tothe entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-11) and the compound represented by theformula (10), the content of the compound represented by the formula(3-11) is preferably 1 mass % or more and 20 mass % or less relative tothe entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-11) and the compound represented by theformula (10), the content of the compound represented by the formula(10) is preferably 80 mass % or more and 99 mass % or less relative tothe entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-21) and the compound represented by theformula (10), the content of the compound represented by the formula(3-21) is preferably 1 mass % or more and 20 mass % or less relative tothe entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-21) and the compound represented by theformula (10), the content of the compound represented by the formula(10) is preferably 80 mass % or more and 99 mass % or less relative tothe entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-31) or (3-32), and the compoundrepresented by the formula (10), the content of the compound representedby the formula (3-31) or (3-32) is preferably 1 mass % or more and 20mass % or less relative to the entire emitting layer.

In one embodiment, when the emitting layer comprises the compoundrepresented by the formula (3-31) or (3-32) and the compound representedby the formula (10), the content of the compound represented by theformula (10) is preferably 80 mass % or more and 99 mass % or lessrelative to the entire emitting layer.

An explanation will be made on the layer configuration of the organic ELdevice according to one aspect of the invention.

An organic EL device according to one aspect of the invention comprisesan organic layer between a pair of electrodes consisting of a cathodeand an anode. The organic layer comprises at least one layer composed ofan organic compound. Alternatively, the organic layer is formed bylaminating a plurality of layers composed of an organic compound. Theorganic layer may further comprise an inorganic compound in addition tothe organic compound.

In one embodiment, at least one of the organic layers is an emittinglayer. The organic layer may be constituted, for example, as a singleemitting layer, or may comprise other layers which can be adopted in thelayer structure of the organic EL device. The layer that can be adoptedin the layer structure of the organic EL device is not particularlylimited, but examples thereof include a hole-transporting zone (ahole-transporting layer, a hole-injecting layer, an electron-blockinglayer, an exciton-blocking layer, etc.), an emitting layer, a spacinglayer, and an electron-transporting zone (electron-transporting layer,electron-injecting layer, hole-blocking layer, etc.) provided betweenthe cathode and the emitting layer.

The organic EL device according to one aspect of the invention may be,for example, a fluorescent or phosphorescent monochromatic lightemitting device or a fluorescent/phosphorescent hybrid white lightemitting device. Further, it may be a simple type device having a singleemitting unit or a tandem type device having a plurality of emittingunits.

The “emitting unit” in the specification is the smallest unit thatcomprises organic layers, in which at least one of the organic layers isan emitting layer and light is emitted by recombination of injectedholes and electrons.

In addition, the “emitting layer” described in the present specificationis an organic layer having an emitting function. The emitting layer is,for example, a phosphorescent emitting layer, a fluorescent emittinglayer or the like, and may be a single layer or a stack of a pluralityof layers.

The emitting unit may be a stacked type unit having a plurality ofphosphorescent emitting layers or fluorescent emitting layers. In thiscase, for example, a spacing layer for preventing excitons generated inthe phosphorescent emitting layer from diffusing into the fluorescentemitting layer may be provided between the respective light-emittinglayers.

As the simple type organic EL device, a device configuration such asanode/emitting unit/cathode can be given.

The representative layer structure of the emitting unit is shown below.The layers in parentheses are provided arbitrarily.

-   -   (a) (Hole-injecting layer/) Hole-transporting layer/Fluorescent        emitting layer (/Electron-transporting layer/Electron-injecting        layer)    -   (b) (Hole-injecting layer/) Hole-transporting        layer/Phosphorescent emitting layer (/Electron-transporting        layer/Electron-injecting layer)    -   (c) (Hole-injecting layer/) Hole-transporting layer/First        fluorescent emitting layer/Second fluorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (d) (Hole-injecting layer/) Hole-transporting layer/First        phosphorescent layer/Second phosphorescent layer        (/Electron-transporting layer/Electron-injecting layer)    -   (e) (Hole-injecting layer/) Hole-transporting        layer/Phosphorescent emitting layer/Spacing layer/Fluorescent        emitting layer (/Electron-transporting layer/Electron-injecting        layer)    -   (f) (Hole-injecting layer/) Hole-transporting layer/First        phosphorescent emitting layer/Second phosphorescent emitting        layer/Spacing layer/Fluorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (g) (Hole-injecting layer/) Hole-transporting layer/First        phosphorescent layer/Spacing layer/Second phosphorescent        emitting layer/Spacing layer/Fluorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (h) (Hole-injecting layer/) Hole-transporting        layer/Phosphorescent emitting layer/Spacing layer/First        fluorescent emitting layer/Second fluorescent emitting layer        (/Electron-transporting Layer/Electron-injecting Layer)    -   (i) (Hole-injecting layer/) Hole-transporting        layer/Electron-blocking layer/Fluorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (j) (Hole-injecting layer/) Hole-transporting        layer/Electron-blocking layer/Phosphorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (k) (Hole-injecting layer/) Hole-transporting        layer/Exciton-blocking layer/Fluorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (l) (Hole-injecting layer/) Hole-transporting        layer/Exciton-blocking layer/Phosphorescent emitting layer        (/Electron-transporting layer/Electron-injecting layer)    -   (m) (Hole-injecting layer/) First hole-transporting Layer/Second        hole-transporting Layer/Fluorescent emitting layer        (/Electron-transporting layer/electron-injecting Layer)    -   (n) (Hole-injecting layer/) First hole-transporting layer/Second        hole-transporting layer/fluorescent emitting layer (/First        electron-transporting layer/Second electron-transporting        layer/Electron-injection layer)    -   (o) (Hole-injecting layer/) First hole-transporting layer/Second        hole-transporting layer/Phosphorescent emitting layer        (/Electron-transporting layer/Electron-injecting Layer)    -   (p) (Hole-injecting layer/) First hole-transporting layer/Second        hole-transporting layer/Phosphorescent emitting layer (/First        electron-transporting Layer/Second electron-transporting        layer/Electron-injecting layer)    -   (q) (Hole-injecting layer/) Hole-transporting layer/Fluorescent        emitting layer/Hole-blocking layer (/Electron-transporting        layer/Electron-injecting layer)    -   (r) (Hole-injecting layer) Hole-transporting        layer/Phosphorescent emitting layer/Hole-blocking        layer(/Electron-transport layer/Electron-injecting layer)    -   (s) (Hole-injecting layer/) Hole-transporting layer/Fluorescent        emitting layer/Exciton-blocking layer (/Electron-transporting        layer/Electron-injecting layer)    -   (t) (Hole-injecting layer/) Hole-transporting        layer/Phosphorescent emitting layer/Exciton-blocking layer        (/Electron-transporting layer/Electron-injecting layer)

The layer structure of the organic EL device according to one aspect ofthe invention is not limited thereto. For example, when the organic ELdevice has a hole-injecting layer and a hole-transporting layer, it ispreferred that a hole-injecting layer be provided between thehole-transporting layer and the anode. Further, when the organic ELdevice has an electron-injecting layer and an electron-transportinglayer, it is preferred that an electron-injecting layer be providedbetween the electron-transporting layer and the cathode. Further, eachof the hole-injecting layer, the hole-transporting layer, theelectron-transporting layer and the electron-injecting layer may beformed of a single layer or be formed of a plurality of layers.

The plurality of phosphorescent emitting layers, and the plurality ofthe phosphorescent emitting layer and the fluorescent emitting layer maybe emitting layers that emit mutually different colors. For example, theemitting unit (f) may include a hole-transporting layer/firstphosphorescent layer (red light emission)/second phosphorescent emittinglayer (green light emission)/spacing layer/fluorescent emitting layer(blue light emission)/electron-transporting layer.

An electron-blocking layer may be provided between each light emittinglayer and the hole-transporting layer or the spacing layer. Further, ahole-blocking layer may be provided between each emitting layer and theelectron-transporting layer. By providing the electron-blocking layer orthe hole-blocking layer, it is possible to confine electrons or holes inthe emitting layer, thereby to improve the recombination probability ofcarriers in the emitting layer, and to improve light emittingefficiency.

As a representative device configuration of a tandem type organic ELdevice, for example, a device configuration such as anode/first emittingunit/intermediate layer/second emitting unit/cathode can be given.

The first emitting unit and the second emitting unit are independentlyselected from the above-mentioned emitting units, for example.

The intermediate layer is also generally referred to as an intermediateelectrode, an intermediate conductive layer, a charge generating layer,an electron withdrawing layer, a connecting layer, a connector layer, oran intermediate insulating layer. The intermediate layer is a layer thatsupplies electrons to the first emitting unit and holes to the secondemitting unit, and can be formed from known materials.

FIG. 1 shows a schematic view of one example of the layer structure ofthe organic EL device. An organic EL device 1 has a substrate 2, ananode 3, a cathode 4, and an emitting unit (organic layer) 10 arrangedbetween the anode 3 and the cathode 4. The emitting unit 10 has at leastone emitting layer 5.

A hole-transporting zone (hole-injecting layer, hole-transporting layer,etc.) 6 may be formed between the emitting layer 5 and the anode 3, andan electron-transporting zone (electron-injecting layer,electron-transporting layer, etc.) 7 may be formed between the emittinglayer 5 and the cathode 4. An electron-blocking layer (not shown) may beprovided on the anode 3 side of the emitting layer 5, and ahole-blocking layer (not shown) may be provided on the cathode 4 side ofthe emitting layer 5. Due to such a configuration, electrons or holesare confined in the emitting layer 5, whereby efficiency of formation ofexcitons in the emitting layer 5 can be further enhanced.

FIG. 2 shows a schematic view of another example of the layerconfiguration of the organic EL device. In an organic EL device 11 shownin FIG. 2 , in an emitting unit 20, the hole-transporting layer in thehole-transporting zone 6 and the electron-transporting layer in theelectron-transporting zone 7 of the emitting unit 10 of the organic ELdevice 1 in FIG. 1 are respectively composed of two layers. Thehole-transporting zone 6 has a first hole-transporting layer 6 a on theanode side and a second hole-transporting layer 6 b on the cathode side.The electron-transporting zone 7 has a first electron-transporting layer7 a on the anode side and a second hole-transporting layer 7 b on thecathode side. As for the other numerical references, since they are thesame as those in FIG. 1 , an explanation is omitted.

Hereinbelow, an explanation will be made on function, materials, etc. ofeach layer constituting the organic EL device described in the presentspecification.

(Substrate)

The substrate is used as a support of the organic EL device. Thesubstrate preferably has a light transmittance of 50% or more in thevisible light region with a wavelength of 400 to 700 nm, and a smoothsubstrate is preferable. Examples of the material of the substrateinclude soda-lime glass, aluminosilicate glass, quartz glass, plasticand the like. As a substrate, a flexible substrate can be used. Theflexible substrate means a substrate that can be bent (flexible), andexamples thereof include a plastic substrate and the like. Specificexamples of the material for forming the plastic substrate includepolycarbonate, polyallylate, polyether sulfone, polypropylene,polyester, polyvinyl fluoride, polyvinyl chloride, polyimide,polyethylene naphthalate and the like. Also, an inorganic vapordeposited film can be used.

(Anode)

As the anode, for example, it is preferable to use a metal, an alloy, aconductive compound, a mixture thereof or the like and having a highwork function (specifically, 4.0 eV or more). Specific examples of thematerial of the anode include indium oxide-tin oxide (ITO: Indium TinOxide), indium oxide-tin oxide containing silicon or silicon oxide,indium oxide-zinc oxide, indium oxide containing tungsten oxide or zincoxide, graphene and the like. In addition, it is also possible to usegold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron,cobalt, copper, palladium, titanium, and nitrides of these metals (e.g.titanium oxide).

The anode is normally formed by depositing these materials on thesubstrate by a sputtering method. For example, indium oxide-zinc oxidecan be formed by a sputtering method by using a target in which 1 to 10mass % zinc oxide is added relative to indium oxide. Further, indiumoxide containing tungsten oxide or zinc oxide can be formed by asputtering method by using a target in which 0.5 to 5 mass % of tungstenoxide or 0.1 to 1 mass % of zinc oxide is added relative to indiumoxide.

As the other methods for forming the anode, a vacuum deposition method,a coating method, an inkjet method, a spin coating method or the likecan be given. When silver paste or the like is used, it is possible touse a coating method, an inkjet method or the like.

The hole-injecting layer formed in contact with the anode is formed byusing a material that allows easy hole injection regardless of the workfunction of the anode. For this reason, in the anode, it is possible touse a common electrode material, e.g. a metal, an alloy, a conductivecompound and a mixture thereof. Specifically, a material having a smallwork function such as alkaline metals such as lithium and cesium;alkaline earth metals such as calcium and strontium; alloys containingthese metals (for example, magnesium-silver and aluminum-lithium); rareearth metals such as europium and ytterbium; and an alloy containingrare earth metals.

(Hole-Injecting Layer)

A hole-injecting layer is a layer that contains a substance having highhole-injection property and has a function of injecting holes from theanode to the organic layer. As the substance having high hole-injectionproperty, molybdenum oxide, titanium oxide, vanadium oxide, rheniumoxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide,tantalum oxide, silver oxide, tungsten oxide, manganese oxide, anaromatic amine compound, an electron-attracting (acceptor) compound or apolymeric compound (oligomer, dendrimer, polymer, etc.) or the like canbe used. Among these, a compound such as an aromatic amine compound andan acceptor compound are preferable, with an acceptor compound beingmore preferable.

As specific examples of an aromatic amine compound,4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA),4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino] biphenyl(abbreviation: DPAB),4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl(abbreviation: DNTPD),1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene(abbreviation: DPA3B),3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA1),3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA2),3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole(abbreviation: PCzPCN1) or the like can be given.

As the acceptor compound, for example, a heterocyclic derivative havingan electron attracting group, a quinone derivative having an electronattracting group, an aryl borane derivative, a heteroaryl boranederivative and the like are preferable. As specific examples,hexacyanohexaazatriphenylene,2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation:F4TCNQ),1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropaneor the like can be given.

When the acceptor compound is used, it is preferred that thehole-injecting layer further comprise a matrix material. As the matrixmaterial, a material known as the material for an organic EL device canbe used. For example, an electron-donating (donor) compound can be used.More preferably, the above-mentioned aromatic amine compound can beused.

(Hole-Transporting Layer)

The hole-transporting layer is a layer that comprises a highhole-transporting property, and has a function of transporting holesfrom the anode to the organic layer.

As the substance having a high hole-transporting property, a materialhaving a hole mobility of 10⁻⁶ cm²/(V·s) or more is preferable. Forexample, aromatic amine compounds, carbazole derivatives, anthracenederivatives, polymeric compounds, and the like can be given, forexample.

Specific examples of the aromatic amine compound include4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine(abbreviation: BAFLP),4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine(abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA),4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB) or the like.

Specific examples of the carbazole derivatives include4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP),9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA),9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA) or the like.

Specific examples of the anthracene derivative include2-t-butyl-9,10-di(2-naphthyl) anthracene (abbreviation: t-BuDNA),9,10-di(2-naphthyl)anthracene (abbreviation: DNA)9,10-diphenylanthracene (abbreviation: DPAnth) or the like.

Specific examples of the polymeric compound includepoly(N-vinylcarbazole) (abbreviation: PVK) andpoly(4-vinyltriphenylamine) (abbreviation: PVTPA).

As long as it is a compound having a higher hole-transporting propertyas compared with electron-transporting property, other substances thanthose mentioned above can be used.

The hole-transporting layer may be a single layer or may be a stackedlayer of two or more layers. In this case, it is preferred that a layerthat contains a substance having a larger energy gap among substanceshaving higher hole-transporting property be arranged on a side nearer tothe emitting layer.

(Emitting Layer)

The emitting layer is a layer containing a substance having a highemitting property (dopant material). As the dopant material, variousmaterials can be used. For example, a fluorescent emitting compound(fluorescent dopant), a phosphorescent emitting compound (phosphorescentdopant) or the like can be used. A fluorescent emitting compound is acompound capable of emitting light from the singlet excited state, andan emitting layer containing a fluorescent emitting compound is called afluorescent emitting layer. Further, a phosphorescent emitting compoundis a compound capable of emitting light from the triplet excited state,and an emitting layer containing a phosphorescent emitting compound iscalled a phosphorescent emitting layer.

The emitting layer normally comprises a dopant material and a hostmaterial that allows it to emit light efficiently. In some literatures,a dopant material is called a guest material, an emitter or an emittingmaterial. In some literatures, a host material is called a matrixmaterial.

A single emitting layer may comprise plural dopant materials and pluralhost materials. Further, plural emitting layers may be present.

In the present specification, a host material combined with thefluorescent dopant is referred to as a “fluorescent host” and a hostmaterial combined with the phosphorescent dopant is referred to as the“phosphorescent host”. Note that the fluorescent host and thephosphorescent host are not classified only by the molecular structure.The phosphorescent host is a material for forming a phosphorescentemitting layer containing a phosphorescent dopant, but does not meanthat it cannot be used as a material for forming a fluorescent emittinglayer. The same can be applied to the fluorescent host.

In one embodiment, it is preferred that the emitting layer comprise thecompound represented by the formulas (1-1) and (1-3) or the compoundrepresented by the formulas (1-2) and (1-3) (hereinafter, thesecompounds may be referred to as the “compound (1)”). More preferably, itis contained as a dopant material. Further, it is preferred that thecompound (1) be contained in the emitting layer as the fluorescentdopant.

In one embodiment, no specific restrictions are imposed on the contentof the compound (1) as the dopant material in the emitting layer. Inrespect of sufficient emission and concentration quenching, the contentis preferably 0.1 to 70 mass %, more preferably 0.1 to 30 mass %,further preferably 1 to 30 mass %, still further preferably 1 to 20 mass%, and particularly preferably 1 to 10 mass %.

In one embodiment, it is preferred that the emitting layer comprise thecompound represented by the formula (3-11). More preferably, it iscontained as a dopant material. Further, it is preferred that thecompound (3-11) be contained in the emitting layer as the fluorescentdopant.

In one embodiment, no specific restrictions are imposed on the contentof the compound represented by the formula (3-11) as the dopant materialin the emitting layer. In respect of sufficient emission andconcentration quenching, the content is preferably 0.1 to 70 mass %,more preferably 0.1 to 30 mass %, further preferably 1 to 30 mass %,still further preferably 1 to 20 mass %, and particularly preferably 1to 10 mass %.

In one embodiment, it is preferred that the emitting layer comprise thecompound represented by the formula (3-21). More preferably, it iscontained as a dopant material. Further, it is preferred that thecompound (3-21) be contained in the emitting layer as the fluorescentdopant.

In one embodiment, no specific restrictions are imposed on the contentof the compound represented by the formula (3-21) as the dopant materialin the emitting layer. In respect of sufficient emission andconcentration quenching, the content is preferably 0.1 to 70 mass %,more preferably 0.1 to 30 mass %, further preferably 1 to 30 mass %,still further preferably 1 to 20 mass %, and particularly preferably 1to 10 mass %.

In one embodiment, it is preferred that the emitting layer comprise thecompound represented by the formula (3-31) or (3-32). More preferably,it is contained as a dopant material. Further, it is preferred that thecompound (3-31) or (3-32) be contained in the emitting layer as thefluorescent dopant.

In one embodiment, no specific restrictions are imposed on the contentof the compound (3-31) or (3-32) as the dopant material in the emittinglayer. In respect of sufficient emission and concentration quenching,the content is preferably 0.1 to 70 mass %, more preferably 0.1 to 30mass %, further preferably 1 to 30 mass %, still further preferably 1 to20 mass %, and particularly preferably 1 to 10 mass %.

(Fluorescent Dopant)

As the fluorescent dopant other than the compound (1), the compoundrepresented by the formula (3-11), the compound represented by theformula (3-21) and the compound represented by the formula (3-31) or(3-32), a fused polycyclic aromatic derivative, a styrylaminederivative, a fused ring amine derivative, a boron-containing compound,a pyrrole derivative, an indole derivative, a carbazole derivative canbe given, for example. Among these, a fused ring amine derivative, aboron-containing compound, carbazole derivative is preferable.

As the fused ring amine derivative, a diaminopyrene derivative, adiaminochrysene derivative, a diaminoanthracene derivative, adiaminofluorene derivative, a diaminofluorene derivative with which oneor more benzofuro skeletons are fused, or the like can be given.

As the boron-containing compound, a pyrromethene derivative, atriphenylborane derivative or the like can be given.

As the blue fluorescent dopant, pyrene derivatives, styrylaminederivatives, chrysene derivatives, fluoranthene derivatives, fluorenederivatives, diamine derivatives, triarylamine derivatives and the likecan be given, for example. Specifically,N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(abbreviation: YGA2S),4-(9H-carbazol-9-yl)-4′-(10-phenyl-9-anthryl)triphenyamine(abbreviation: YGAPA),4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine(abbreviation: PCBAPA) or the like can be given.

As the green fluorescent dopant, an aromatic amine derivative or thelike can be given, for example. Specifically,N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine(abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine(abbreviation: DPhAPhA) or the like can be given, for example.

As the red fluorescent dopant, a tetracene derivative, a diaminederivative or the like can be given. Specifically,N,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation:p-mPhTD),7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine(abbreviation: p-mPhAFD) or the like can be given.

(Phosphorescent Dopant)

As the phosphorescent dopant, a phosphorescent emitting heavy metalcomplex and a phosphorescent emitting rare earth metal complex can begiven.

As the heavy metal complex, an iridium complex, an osmium complex, aplatinum complex or the like can be given. As the heavy metal complex,an ortho-metalated complex of a metal selected from iridium, osmium andplatinum.

Examples of rare earth metal complexes include terbium complexes,europium complexes and the like. Specifically,tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation:Tb(acac)₃(Phen)),tris(1,3-diphenyl-1,3-propandionate)(monophenanthroline)europium(III)(abbreviation: Eu(DBM)₃(Phen)),tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III)(abbreviation: Eu(TTA)₃(Phen)) or the like can be given. These rareearth metal complexes are preferable as phosphorescent dopants sincerare earth metal ions emit light due to electronic transition betweendifferent multiplicity.

As the blue phosphorescent dopant, an iridium complex, an osmiumcomplex, a platinum complex, or the like can be given, for example.Specifically, bis[2-(4′,6′-difluorophenyl)pyridinate-N,C2′]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: Fir6),bis[2-(4′,6′-difluorophenyl)pyridinate-N,C2′]iridium(III) picolinate(abbreviation: Flrpic), bis[2-(3′,5′-bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III) picolinate (abbreviation:Ir(CF₃ppy)₂(pic)),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)acetylacetonate (abbreviation: Flracac) or the like can be given.

As the green phosphorescent dopant, an iridium complex or the like canbe given, for example. Specifically, tris(2-phenylpyridinato-N,C2′)iridium(III) (abbreviation: Ir(ppy)₃),bis(2-phenylpyridinato-N,C2′)iridium(III) acetylacetonate (abbreviation:Ir(ppy)₂(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonate (abbreviation: Ir(pbi)₂(acac)),bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation:Ir(bzq)₂(acac)) or the like can be given.

As the red phosphorescent dopant, an iridium complex, a platinumcomplex, a terbium complex, an europium complex or the like can begiven. Specifically,bis[2-(2′-benzo[4,5-a]thienyl)pyridinato-N,C3′]iridium(III)acetylacetonate (abbreviation: Ir(btp)₂(acac)),bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonate(abbreviation: Ir(piq)₂(acac)),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III)(abbreviation: Ir(Fdpq)₂(acac)),2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II)(abbreviation PtOEP) or the like can be given.

(Host Material)

As the host material, metal complexes such as aluminum complexes,beryllium complexes and zinc complexes; heterocyclic compounds such asindole derivatives, pyridine derivatives, pyrimidine derivatives,triazine derivatives, quinoline derivatives, isoquinoline derivatives,quinazoline derivatives, dibenzofuran derivatives, dibenzothiophenederivatives, oxadiazole derivatives, benzimidazole derivatives,phenanthroline derivatives; fused aromatic compounds such as anaphthalene derivative, a triphenylene derivative, a carbazolederivative, an anthracene derivative, a phenanthrene derivative, apyrene derivative, a chrysene derivative, a naphthacene derivative, afluoranthene derivative; and aromatic amine compound such astriarylamine derivatives and fused polycyclic aromatic amine derivativescan be given, for example. Plural types of host materials can be used incombination.

As specific examples of the metal complex,tris(8-quinolinolato)aluminum(III) (abbreviation: Alq),tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3),bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO),bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviation: ZnBTZ) or thelike can be given.

As specific examples of the heterocyclic compound,2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzoimidazole)(abbreviation:TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin(abbreviation: BCP) or the like can be given.

As specific examples of the fused aromatic compound,9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole(abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene(abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,9′-bianthryl (abbreviation: BANT),9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2),3,3′,3″-(benzene-1,3,5-triyl)tripyene (abbreviation: TPB3),9,10-diphenylanthracene (abbreviation: DPAnth),6,12-dimethoxy-5,11-diphenylcrysene or the like can be given.

As specific examples of the aromatic amine compound,N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine(abbreviation: DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine(abbreviation: PCAPBA),N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(abbreviation: NPB or α-NPD), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD),4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi),4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB) or the like can be given.

As the fluorescent host, a compound having a higher singlet energy levelthan a fluorescent dopant is preferable. For example, a heterocycliccompound, a fused aromatic compound or the like can be given. As thefused aromatic compound, an anthracene derivative, a pyrene derivative,a chrysene derivative, a naphthacene derivative or the like arepreferable.

As the phosphorescent host, a compound having a higher triplet energylevel as compared with a phosphorescent dopant is preferable. Forexample, a metal complex, a heterocyclic compound, a fused aromaticcompound or the like can be given. Among these, an indole derivative, acarbazole derivative, a pyridine derivative, a pyrimidine derivative, atriazine derivative, a quinolone derivative, an isoquinoline derivative,a quinazoline derivative, a dibenzofuran derivative, a dibenzothiophenederivative, a naphthalene derivative, a triphenylene derivative, aphenanthrene derivative, a fluoranthene derivative or the like can begiven.

(Electron-Transporting Layer)

An electron-transporting layer is a layer that comprises a substancehaving high electron-transporting property. As the substance having highelectron-transporting property, a substance having an electron mobilityof 10⁻⁶ cm²N/s or more is preferable. For example, a metal complex, anaromatic heterocyclic compound, an aromatic hydrocarbon compound, apolymeric compound or the like can be given.

As the metal complex, an aluminum complex, a beryllium complex, a zinccomplex or the like can be given. Specifically,tris(8-quinolinolate)aluminum(III) (abbreviation: Alq),tris(4-methyl-8-quinolinolate)aluminum (abbreviation: Almq3),bis(10-hydroxybenzo[h]quinolinolate)beryllium (abbreviation: BeBq2),bis(2-methyl-8-quinollinolate)(4-phenylphenolate)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolate)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO),bis[2-(2-benzothiazolyl phenolato]zinc(II) (abbreviation: ZnBTZ) or thelike can be given, for example.

As the aromatic heterocyclic compound, imidazole derivatives such asbenzimidazole derivatives, imidazopyridine derivatives andbenzimidazophenanthridine derivatives; azine derivatives such aspyrimidine derivatives and triazine derivatives; a compound containing anirogen-containing six-membered ring structure such as quinolinederivatives, isoquinoline derivatives, and phenanthroline derivatives(including one having a phosphine oxide-based substituent on theheterocyclic ring) or the like can be given. Specifically,2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene(abbreviation: OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen),bathocuproin (abbreviation: BCP),4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) or thelike can be given.

As the aromatic hydrocarbon compound, an anthracene derivative, afluoranthene derivative or the like can be given, for example.

As specific examples of the polymeric compound,poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation:PF-Py),poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](abbreviation: PF-BPy) or the like can be given.

As long as it is a compound having a higher electron-transportingproperty as compared with hole-transporting property, such a compoundmay be used in the electron-transporting layer in addition to thesubstances mentioned above.

The electron-transporting layer may be a single layer, or a stackedlayer of two or more layers. In this case, it is preferable to arrange alayer that includes a substance having a larger energy gap, amongsubstances having a high electron-transporting capability, on the sidenearer to the emitting layer.

For example, as shown in FIG. 2 , a configuration including the firstelectron-transporting layer 7 a on the anode side and the secondelectron-transporting layer 7 b on the cathode side may be employed.

The electron-transporting layer may contain a metal such as an alkalimetal, magnesium, an alkaline earth metal, or an alloy containing two ormore of these metals; a metal compound such as an alkali metal compoundsuch as 8-quinolinolato lithium (Liq), or an alkaline earth metalcompound.

When a metal such as an alkali metal, magnesium, an alkaline earthmetal, or an alloy containing two or more of these metals is containedin the electron-transporting layer, the content of the metal is notparticularly limited, but is preferably from 0.1 to 50 mass %, morepreferably from 0.1 to 20 mass %, further preferably from 1 to 10 mass%.

When a metal compound such as an alkali metal compound or an alkalineearth metal compound is contained in the electron-transporting layer,the content of the metal compound is preferably 1 to 99 mass %, morepreferably from 10 to 90 mass %. When the electron-transporting layer isformed of plural layers, a layer on the emitting layer side can beformed only from these metal compounds.

(Electron-Injecting Layer)

The electron-injecting layer is a layer that includes a substance thathas a high electron-injecting capability, and has the function ofefficiently injecting electrons from a cathode to an emitting layer.Examples of the substance that has a high electron-injecting capabilityinclude an alkali metal, magnesium, an alkaline earth metal, and acompound thereof. Specific examples thereof include lithium, cesium,calcium, lithium fluoride, cesium fluoride, calcium fluoride, lithiumoxide, and the like. In addition, an electron-transporting substancehaving electron-transporting property in which is incorporated with analkali metal, magnesium, an alkaline earth metal, or a compound thereofis incorporated, for example, Alq incorporated with magnesium, may alsobe used.

Alternatively, a composite material that includes an organic compoundand a donor compound may also be used in the electron-injecting layer.Such a composite material is excellent in the electron-injectingcapability and the electron-transporting capability since the organiccompound receives electrons from the donor compound.

The organic compound is preferably a material excellent in transportingcapability of the received electrons, and specifically, for example, ametal complex, an aromatic heterocyclic compound, or the like, which isa substance that has a high electron-transporting capability mentionedabove, can be used.

Any material capable of donating its electron to the organic compoundcan be used as the donor compound. Examples thereof include an alkalimetal, magnesium, an alkaline earth metal, and a rare earth metal.Specific examples thereof include lithium, cesium, magnesium, calcium,erbium, and ytterbium. Further, an alkali metal oxide and an alkalineearth metal oxide are preferred, and examples thereof include lithiumoxide, calcium oxide, and barium oxide. In addition, a Lewis base suchas magnesium oxide can be used. Moreover, an organic compound such astetrathiafulvalene (abbreviation: TTF) can also be used.

(Cathode)

For the cathode, a metal, an alloy, an electrically conductive compound,and a mixture thereof, each having a small work function (specifically,a work function of 3.8 eV or less) are preferably used. Specificexamples of the material for such a cathode include an alkali metal suchas lithium and cesium; magnesium; an alkaline earth metal such ascalcium, and strontium; an alloy containing these metals (for example,magnesium-silver, aluminum-lithium); a rare earth metal such as europiumand ytterbium; and an alloy containing a rare earth metal.

The cathode is usually formed by a vacuum vapor deposition or asputtering method. Further, in the case of using a silver paste or thelike, a coating method, an inkjet method, or the like can be employed.

Moreover, when the electron-injecting layer is provided, variouselectrically conductive materials such as aluminum, silver, ITO,graphene, indium oxide-tin oxide containing silicon or silicon oxide,selected independently from the work function, can be used to form acathode. These electrically conductive materials are made into filmsusing a sputtering method, an inkjet method, a spin coating method, orthe like.

(Insulating Layer)

In the organic EL device, pixel defects based on leakage or a shortcircuit are easily generated since an electric field is applied to athin film. In order to prevent this, it is preferred to insert aninsulating thin layer between a pair of electrodes.

Examples of materials used in the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. A mixture thereof may be used in the insulating layer,and a laminate of a plurality of layers that include these materials canbe also used for the insulating layer.

(Spacing Layer)

The spacing layer is a layer provided between the fluorescent emittinglayer and the phosphorescent emitting layer when the fluorescentemitting layer and the phosphorescent emitting layer are stacked inorder to prevent diffusion of excitons generated in the phosphorescentemitting layer to the fluorescent emitting layer or in order to adjustthe carrier balance. Further, the spacing layer can be provided betweenthe plural phosphorescent emitting layers.

Since the spacing layer is provided between the emitting layers, thematerial used for the spacing layer is preferably a material having bothelectron-transporting capability and hole-transporting capability. Inorder to prevent diffusion of the triplet energy in adjacentphosphorescent emitting layers, it is preferred that the spacing layerhave a triplet energy of 2.6 eV or more.

As the material used for the spacing layer, the same materials as thoseused in the above-mentioned hole-transporting layer can be given.

(Electron-Blocking Layer, Hole-Blocking Layer, Exciton-Blocking Layer)

An electron-blocking layer, a hole-blocking layer, an exciton(triplet)-blocking layer, and the like may be provided in adjacent tothe emitting layer.

The electron-blocking layer has a function of preventing leakage ofelectrons from the emitting layer to the hole-transporting layer. Thehole-blocking layer has a function of preventing leakage of holes fromthe emitting layer to the electron-transporting layer. Theexciton-blocking layer has a function of preventing diffusion ofexcitons generated in the emitting layer to the adjacent layers andconfining the excitons within the emitting layer.

(Method for Forming a Layer)

The method for forming each layer of the organic EL device of theinvention is not particularly limited unless otherwise specified. Aknown film-forming method such as a dry film-forming method, a wetfilm-forming method or the like can be used. Specific examples of thedry film-forming method include a vacuum deposition method, a sputteringmethod, a plasma method, an ion plating method, and the like. Specificexamples of the wet film-forming method include various coating methodssuch as a spin coating method, a dipping method, a flow coating method,an inkjet method, and the like.

(Film Thickness)

The film thickness of each layer of the organic EL device of theinvention is not particularly limited unless otherwise specified. If thefilm thickness is too small, defects such as pinholes are likely tooccur to make it difficult to obtain a sufficient luminance. If the filmthickness is too large, a high driving voltage is required to beapplied, leading to a lowering in efficiency. In this respect, the filmthickness is preferably 5 nm to 10 μm, and more preferably 10 nm to 0.2μm.

[Electronic Apparatus]

The electronic apparatus according to one aspect of the inventionincludes the above-described organic EL device according to one aspectof the invention. Examples of the electronic apparatus include displayparts such as an organic EL panel module; display devices of televisionsets, mobile phones, smart phones, and personal computer, and the like;and emitting devices of a lighting device and a vehicle lighting device.

[Novel Compound]

The novel compound according to one aspect of the invention is acompound represented by the following formulas (1-1) and (1-3), or thecompound represented by the following formulas (1-2) and (1-3):

wherein in the formulas (1-1), (1-2) and (1-3),

-   -   ring A is a substituted or unsubstituted fused aryl ring        including 10 to 50 ring carbon atoms, a substituted or        unsubstituted fused heterocyclic ring including 8 to 50 ring        atoms or a benzene ring represented by the following formula        (2);    -   two atomic bondings * in the formula (1-1) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   three atomic bondings * in the formula (1-2) are respectively        bonded with a ring carbon atom of the fused aryl ring of the        ring A, a ring atom of the fused heterocyclic ring of the ring        A, or a ring carbon atom of the benzene ring represented by the        formula (2) of the ring A;    -   one or more pairs of adjacent two or more of R₁ to R₁₆ may form        a substituted or unsubstituted, saturated or unsaturated ring;    -   R₁ to R₁₆ that do not form the substituted or unsubstituted,        saturated or unsaturated ring are independently a hydrogen atom,        a substituted or unsubstituted alkyl group including 1 to 50        carbon atoms, a substituted or unsubstituted haloalkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkenyl group including 2 to 50 carbon atoms, a substituted or        unsubstituted alkynyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted alkoxy group        including 1 to 50 carbon atoms, a substituted or unsubstituted        alkylthio group including 1 to 50 carbon atoms, a substituted or        unsubstituted aryloxy group including 6 to 50 ring carbon atoms,        a substituted or unsubstituted arylthio group including 6 to 50        ring carbon atoms, a substituted or unsubstituted aralkyl group        including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄,        —COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro        group, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when the ring A is a benzene ring represented by the formula        (2), at least one of R₁ to R₁₇ is a substituted or unsubstituted        alkyl group including 1 to 50 carbon atoms, a substituted or        unsubstituted cycloalkyl group including 3 to 50 ring carbon        atoms, a substituted or unsubstituted aryl group including 6 to        50 ring carbon atoms, or a substituted or unsubstituted        monovalent heterocyclic group including 5 to 50 ring atoms; or        at least one pair of adjacent two or more of R₁ to R₁₆ forms a        substituted or unsubstituted, saturated or unsaturated ring; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different;

-   -   wherein in the formula (2), at one of the two ring carbon atoms        indicated by the atomic bonding extending from the benzene ring        B in the formula (1-1) or the formula (1-2) is bonded, and at        the other of the two ring carbon atoms indicated by *, the        atomic bonding extending from the benzene ring C in the formula        (1-3) is bonded;    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms;    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different; and    -   n is an integer of 1 or 2, and when n is 2, two R₁₇s may be the        same or different.

In the above-mentioned novel compound, if the ring A is a benzene ringrepresented by the formula (2), at least one of R₁ to R₁₇ is asubstituted or unsubstituted alkyl group including 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 50 ringcarbon atoms, a substituted or unsubstituted aryl group including 6 to50 ring carbon atoms, or a substituted or unsubstituted monovalentheterocyclic group including 5 to 50 ring atoms; or at least one pair ofadjacent two or more of R₁ to R₁₆ forms a substituted or unsubstituted,saturated or unsaturated ring.

In this respect, the novel compound according to this aspect isdifferent from the compound represented by the formulas (1-1) and (1-3)and the compound represented by the formula (1-2) and (1-3) contained inthe organic layer of the organic electroluminescence device according toone aspect of the invention described above. On the other hand, thenovel compound according to this aspect is the same except for thisrespect.

Therefore, structures, each substituent, preparation methods in otherembodiments of the novel compound according to this aspect are the sameas those of the compound represented by the formulas (1-1) and (1-3) andthe compound represented by the formula (1-2) and (1-3) contained in theorganic layer of the organic electroluminescence device according to oneaspect of the invention. Furthermore, specific examples thereof includethe same compounds except for the following compounds.

The novel compound according to another aspect of the invention is acompound represented by the following formula (3-11):

-   -   wherein in the formula (3-11),    -   one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ to        R₁₆ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁ to R₇ and R₁₀ to R₁₆ that do not form the substituted or        unsubstituted, saturated or unsaturated ring are independently a        hydrogen atom, a substituted or unsubstituted alkyl group        including 1 to 50 carbon atoms, a substituted or unsubstituted        haloalkyl group including 1 to 50 carbon atoms, a substituted or        unsubstituted alkenyl group including 2 to 50 carbon atoms, a        substituted or unsubstituted alkynyl group including 2 to 50        carbon atoms, a substituted or unsubstituted cycloalkyl group        including 3 to 50 ring carbon atoms, a substituted or        unsubstituted alkoxy group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkylthio group including 1 to 50        carbon atoms, a substituted or unsubstituted aryloxy group        including 6 to 50 ring carbon atoms, a substituted or        unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms, provided that        at least one of R₁ to R₇ and R₁₀ to R₁₆ is —N(R₃₆)(R₃₇);    -   R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl        group including 1 to 50 carbon atoms, a substituted or        unsubstituted haloalkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted alkenyl group including 2 to 50        carbon atoms, a substituted or unsubstituted alkynyl group        including 2 to 50 carbon atoms, a substituted or unsubstituted        cycloalkyl group including 3 to 50 ring carbon atoms, a        substituted or unsubstituted alkoxy group including 1 to 50        carbon atoms, a substituted or unsubstituted alkylthio group        including 1 to 50 carbon atoms, a substituted or unsubstituted        aryloxy group including 6 to 50 ring carbon atoms, a substituted        or unsubstituted arylthio group including 6 to 50 ring carbon        atoms, a substituted or unsubstituted aralkyl group including 7        to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,        —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, a        substituted or unsubstituted aryl group including 6 to 50 ring        carbon atoms or a substituted or unsubstituted monovalent        heterocyclic group including 5 to 50 ring atoms;    -   two R₁₇s may be the same or different;    -   R₃₁ to R₃₇ are independently a hydrogen atom, a substituted or        unsubstituted alkyl group including 1 to 50 carbon atoms, a        substituted or unsubstituted cycloalkyl group including 3 to 50        ring carbon atoms, a substituted or unsubstituted aryl group        including 6 to 50 ring carbon atoms or a substituted or        unsubstituted monovalent heterocyclic group including 5 to 50        ring atoms; and    -   when each of R₃₁ to R₃₇ is present in plural, each of the plural        R₃₁s to R₃₇s may be the same or different.

The above-mentioned novel compound is the same as the compoundrepresented by the formula (3-11) contained in the organic layer of theorganic electroluminescence device according to one aspect of theinvention described above.

Therefore, structures, each substituent, and preparation methods inother embodiments of the novel compound according to this aspect are thesame as those of the compound represented by the formula (3-11)contained in the organic layer of the organic electroluminescence deviceaccording to one aspect of the invention. Furthermore, the same can beapplied to the specific examples of the compound represented by theformula (3-11).

In one embodiment, the compound represented by the formula (3-11) iscompound represented by the following formula (3-13):

-   -   wherein in the formula (3-13),    -   one or more pairs of adjacent two or more of R₁ to R₄ and R₁₀ to        R₁₃ may form a substituted or unsubstituted, saturated or        unsaturated ring;    -   R₁ to R₄, R₁₀ to R₁₃, and R₁₇ that do not form the substituted        or unsubstituted, saturated or unsaturated ring are        independently a hydrogen atom, a substituted or unsubstituted        aryl group including 6 to 18 ring carbon atoms or a substituted        or unsubstituted monovalent heterocyclic group including 5 to 18        ring atoms;    -   two R₁₇s may be the same or different; and    -   R_(A), R_(B), R_(C) and R_(D) are independently a substituted or        unsubstituted aryl group including 6 to 18 ring carbon atoms or        a substituted or unsubstituted monovalent heterocyclic group        including 5 to 18 ring atoms.

The above-mentioned novel compound is the same as the compoundrepresented by the formula (3-13) contained in the organic layer of theorganic electroluminescence device according to one aspect of theinvention described above.

Therefore, structures, each substituent, and preparation methods inother embodiments of the novel compound according to this aspect are thesame as those of the compound represented by the formula (3-13)contained in the organic layer of the organic electroluminescence deviceaccording to one aspect of the invention. Furthermore, the same can beapplied to the specific examples of the compound represented by theformula (3-13).

The novel compound according to another aspect of the invention is acompound represented by the following formula (3-21):

-   -   wherein in the formula (3-21),    -   one or more pairs of adjacent two or more of R₁ to R₄ and R₁₀ to        R₁₃ may form a substituted or unsubstituted, saturated or        unsaturated ring; R₁₇, and R₁ to R₄ and R₁₀ to R₁₃ that do not        form the substituted or unsubstituted, saturated or unsaturated        ring are independently a hydrogen atom, a substituted or        unsubstituted aryl group including 6 to 20 ring carbon atoms or        a substituted or unsubstituted monovalent heterocyclic group        including 5 to 20 ring atoms;    -   two R₁₇s may be the same or different; and    -   R_(A), R_(B), R_(C) and R_(D) are independently a substituted or        unsubstituted aryl group including 6 to 20 ring carbon atoms.

The above-mentioned novel compound is the same as the compoundrepresented by the formula (3-21) contained in the organic layer of theorganic electroluminescence device according to one aspect of theinvention described above.

Therefore, structures, each substituent, and preparation methods inother embodiments of the novel compound according to this aspect are thesame as those of the compound represented by the formula (3-21)contained in the organic layer of the organic electroluminescence deviceaccording to one aspect of the invention. Furthermore, the same can beapplied to the specific examples of the compound represented by theformula (3-21).

The novel compound according to another aspect of the invention is acompound represented by the following formula (3-31) or (3-32):

-   -   wherein in the formula (3-31) and (3-32),    -   one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ to        R₁₆ may form a substituted or unsubstituted, saturated or        unsaturated ring; R₁₇, and R₁ to R₇ and R₁₀ to R₁₆ that do not        form the substituted or unsubstituted, saturated or unsaturated        ring are independently a hydrogen atom, a substituted or        unsubstituted aryl group including 6 to 20 ring carbon atoms or        a substituted or unsubstituted monovalent heterocyclic group        including 5 to 20 ring atoms;    -   two R₁₇s may be the same or different; and    -   Ar₁ to Ar₄ are independently a substituted or unsubstituted aryl        group including 6 to 20 ring carbon atoms.

The above-mentioned novel compound is the same as the compoundrepresented by the formula (3-31) and (3-32) contained in the organiclayer of the organic electroluminescence device according to one aspectof the invention described above.

Therefore, structures, each substituent, and preparation methods inother embodiments of the novel compound according to this aspect are thesame as those of the compound represented by the formula (3-31) and(3-32) contained in the organic layer of the organic electroluminescencedevice according to one aspect of the invention. Furthermore, the samecan be applied to the specific examples of the compound represented bythe formula (3-31) and (3-32).

The novel compounds according to the above aspects are useful as amaterial for organic electroluminescent devices. The novel compoundsaccording to the above aspects are useful as a material of an emittinglayer of an organic electroluminescent device, and is particularlyuseful as a fluorescent emitting material (also referred to as afluorescent dopant) of an emitting layer. The novel compounds accordingto the above aspects can enhance the luminous efficiency of the organicEL device.

EXAMPLES

Next, the invention will be explained in more detail in accordance withthe following synthesis examples, examples, and comparative examples,which should not be construed as limiting the scope of the invention.

Example 1-1 (Fabrication of Organic EL Device)

A glass substrate of 25 mm by 75 mm by 1.1 mm thick with an ITOtransparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning with isopropyl alcohol for 5 minutes,and then subjected to UV-ozone cleaning for 30 minutes. The thickness ofITO was 130 nm.

The cleaned glass substrate with a transparent electrode was mounted ina substrate holder of a vacuum vapor deposition apparatus. First,compound HI was deposited on the surface where the transparent electrodewas formed so as to cover the transparent electrode, thereby to form acompound HI film having a thickness of 5 nm. This HI film functioned asa hole-injecting layer.

Subsequent to the formation of the HI film, compound HT1 was depositedto form an HT1 film in a thickness of 80 nm on the HI film. This HT1film functioned as a first hole-transporting layer.

Subsequent to the formation of the HT1 film, compound HT2 was depositedto form an HT2 film in a thickness of 10 nm on the HT1 film. This HT2film functioned as a second hole-transporting layer.

Compound BH-1 (host material) and compound BD-1 (dopant material) wereco-deposited on the HT2 film so that the ratio (weight ratio) ofcompound BD-1 was 4% to form an emitting layer having a thickness of 25nm.

Compound HBL was deposited on the emitting layer to form anelectron-transporting layer having a thickness of 10 nm. Compound ET(electron-transporting material) was deposited on theelectron-transporting layer to form an electron-injecting layer having athickness of 15 nm. LiF was deposited on the electron-injecting layer toform a LiF film having a thickness of 1 nm. Al metal was deposited onthe LiF film to form a metal cathode having a thickness of 80 nm.

An organic EL device was thus fabricated. The compounds used tofabricate the organic EL device are shown below.

(Evaluation of Organic EL Device)

The initial characteristics of the obtained organic EL device weremeasured at room temperature at 10 mA/cm² of DC (direct current)constant current driving. The measurement results of the voltage areshown in Table 1.

Furthermore, a voltage was applied to the organic EL device so that thecurrent density was 10 mA/cm², and the EL emission spectrum was measuredusing a spectroradiometer “CS-1000” (manufactured by Konica Minolta,Inc.). The external quantum efficiency (EQE) (%) was calculated from theresulting spectral radiance spectrum. The results are shown in Table 1.The numerical values in Table 1 are relative values with the values ofComparative Examples 1-1, 1-2 and 1-3 being each taken to be 100%.

Further, a voltage was applied to the organic EL device so that thecurrent density was 50 mA/cm², and the time (lifetime LT95) until theluminance reached 95% with respect to the initial luminance wasmeasured. The results of the lifetime LT 95 are shown in Table 1.

Examples 1-2 to 1-22 and Comparative Examples 1-1 to 1-3

Using combinations of the dopant materials and the host materials shownin Table 1, organic EL devices were fabricated and evaluated in the samemanner as in Example 1-1. The results are shown in Table 1.

The compounds used are shown below. The compound BD-1 and the compoundBD-2 were synthesized according to the synthesis method described inDibenzo[2,3:5,6]pyrrolizino[1,7-bc]indolo[1,2,3-Im]carbazole: a newelectron donor, New J. Chem., 2010, 34, 1243-1246. Compounds BD-4, BD-9and BD-11 to BD-14 were synthesized by the method described below

TABLE 1 Driving EQE LT95 Host Dopant Voltage (V) (%) (hr) Example 1-1BH-1 BD-1 3.7 135 92 Example 1-2 BD-2 3.7 133 81 Example 1-3 BD-4 3.6146 87 Example 1-4 BD-9 3.7 140 108 Example 1-5 BD-11 3.7 131 95 Example1-6 BD-12 3.7 140 80 Example 1-7 BD-13 3.7 129 94 Example 1-8 BD-14 3.6125 130 Comp. Ex. 1-1 BD-COM 3.7 100 66 Example 1-9 BH-2 BD-1 3.3 144105 Example 1-10 BD-2 3.3 144 94 Example 1-11 BD-4 3.3 150 85 Example1-12 BD-9 3.3 147 102 Example 1-13 BD-11 3.3 145 93 Example 1-14 BD-123.3 154 90 Example 1-15 BD-13 3.3 140 99 Example 1-16 BD-14 3.3 141 105Comp. Ex. 1-2 BD-COM 3.3 100 75 Example 1-17 BH-3 BD-4 3.7 143 95Example 1-18 BD-9 3.7 132 122 Example 1-19 BD-11 3.7 127 100 Example1-20 BD-12 3.7 129 103 Example 1-21 BD-13 3.7 124 105 Example 1-22 BD-143.6 119 139 Comp. Ex. 1-3 BD-COM 3.7 100 70

From the results shown in Table 1, it can be said that BD-1, BD-2, BD-4,BD-9 and BO-11 to BD-14 were ring-fused, and hence, deactivation ofexcitons due to thermal vibration of the compound was suppressed. As aresult, the stability of the compound also increased, so that thecompound had higher efficiency and longer life than those of BD-COM.

Example 2-1

Compound 1 was synthesized by the following synthesis route.

Synthesis of Compound 1-1

Under an argon atmosphere, 3,6-di-tert-butylcarbazole (11.2 g, 40 mmol)was dissolved in chloroform (200 mL), and n-bromosuccinimide (7.12 g)was added thereto, and the mixture was stirred at room temperature for 5hours. After completion of the reaction, the solvent was concentrated,and the residues were purified by column chromatography, wherebyobtaining an amorphous solid (14.4 g). The obtained solid was compound1-1, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 358 with respect to a molecularweight of 358.

Synthesis of Compound 1-2

Under an argon atmosphere, compound 1-1 (14.4 g), bis(pinacolato)diboron(15.2 g, 60 mmol, 1.5 eq.), PdCl₂(dppf) (1.46 g, 2.0 mmol, 5% Pd), andpotassium acetate (7.85 g, 80 mmol) were suspended in dioxane (200 mL),and the mixture was refluxed for 7 hours. After completion of thereaction, the solvent was concentrated by passing through short passsilica gel column chromatography. The resulting solid was recrystallizedfrom hexane/ethyl acetate (9:1) to obtain a white solid (12.1 g, yield:75%). The obtained solid was compound 1-2, which is an intended product,and by mass spectrum analysis, it was confirmed that it had an m/e valueof 405 with respect to a molecular weight of 405.

Synthesis of Compound 1-3

Under an argon atmosphere, dibromodiiodobenzene (4.00 g, 8.20 mmol),compound 1-2 (6.81 g, 16.8 mmol, 1.05 eq.), and Pd(PPh₃)₄(474 mg, 0.41mmol, 5% Pd) were dissolved in 1,2-dimethoxyethane (800 mL) and water(200 mL) in which K₃PO₄ (10.4 g, 49.2 mmol) was dissolved was addedthereto, and the mixture was stirred with heating at 50° C. for 24hours. After completion of the reaction, extraction with ethyl acetatewas conducted, and the solvent was concentrated. The resulting solid waspurified by column chromatography, whereby obtaining a white solid (5.0g, yield: 77%). The obtained solid was compound 1-3, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 790 with respect to a molecular weight of 790.

Synthesis of Compound 1

Under an argon atmosphere, compound 1-3 (2.00 g), Pd₂(dba)₃ (232 mg),SPhos (415 mg), and NaOt-Bu (973 mg) were suspended in xylene (200 mL),and the mixture was refluxed for 8 hours. After completion of thereaction, the resulting mixture was purified by silica gel columnchromatography, whereby obtaining a yellow solid (450 mg, yield: 28%).The obtained solid was compound 1, which is an intended product, and bymass spectrum analysis, it was confirmed that it had an m/e value of 628with respect to a molecular weight of 628.

Example 2-2

Compound BD-4 was synthesized by the following synthesis route.

Synthesis of Intermediate 1

Under an argon atmosphere, 2-iodonitrobenzene (9.7 g, 39 mmol),5-bromo-2-methoxyphenylboronic acid (9.2 g, 40 mmol),tetrakis(triphenylphosphine)palladium(0) (Pd (PPh₃)₄, 1.1 g, 0.975mmol),and K₃PO₄ (21 g, 97 mmol) was dissolved in ethanol (95 mL), andthe mixture was refluxed for 8 hours. After completion of the reaction,the solvent was concentrated, and the residues were purified by columnchromatography, whereby obtaining a yellow solid (8.8 g, yield: 73%).The obtained solid was Intermediate 1, which is an intended product, andby mass spectrum analysis, it was confirmed that it had an r/e value of308 with respect to a molecular weight of 308.

Synthesis of Intermediate 2

Intermediate 1 (7.00 g, 22.7 mmol) was dissolved in o-dichlorobenzene(80 mL), triphenylphosphine (14.9 g, 56.8 mmol) was added thereto, andthe mixture was refluxed for 12 hours. After completion of the reaction,the solvent was concentrated, and the residues were purified by columnchromatography, whereby obtaining a white solid (5.7 g, yield: 78%). Theobtained solid was Intermediate 2, which is an intended product, and bymass spectrum analysis, it was confirmed that it had an m/e value of 276with respect to a molecular weight of 276.

Synthesis of Intermediate 3

Under an argon atmosphere, Intermediate 2 (5.7 g, 21 mmol),pinacolborane (7.9 g, 62 mmol), anddichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (PdCl₂(dppf),1.5 g, 2.0 mmol) was dissolved in dioxane (250 mL), triethylamine (11.5mL, 83 mmol) was added thereto, and the mixture was refluxed for 5hours. After completion of the reaction, the solvent was concentrated,and the residues were purified by column chromatography, wherebyobtaining a yellow solid (5.0 g, yield: 75%). The obtained solid wasIntermediate 3, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 323 with respectto a molecular weight of 323.

Synthesis of Intermediate 4

Under an argon atmosphere, dibromodiiodobenzene (2.5 g, 5.1 mmol),Intermediate 3 (4.97 g, 15.4 mmol), and Pd(PPh₃)₄(237 mg, 0.205 mmol)were dissolved in toluene (250 mL) and dimethylsulfoxide (DMSO, 50 mL),2 M Na₂CO₃ aqueous solution (13 mL) was added thereto, and the mixturewas stirred with heating at 90° C. for 24 hours. After completion of thereaction, toluene was removed under reduced pressure, and theprecipitated solid was filtered off. This solid was washed with methanoland ethyl acetate, whereby obtaining a white solid (2.5 g, yield: 75%).The obtained solid was Intermediate 4, which is an intended product, andby mass spectrum analysis, it was confirmed that it had an m/e value of626 with respect to a molecular weight of 626.

Synthesis of Intermediate 5

Under an argon atmosphere, Intermediate 4 (2.5 g, 3.99 mmol), Cul (76mg, 0.40 mmol), L-proline (92 mg, 0.80 mmol), and K₂CO₃ (1.38 g, 10mmol) were suspended in DMSO (80 mL), and the mixture was stirred withheating at 150° C. for 6 hours. After completion of the reaction, theprecipitated solid was filtered off. This solid was washed with methanoland ethyl acetate, whereby obtaining a brown solid (1.4 g, yield: 75%).The obtained solid was Intermediate 5, which is an intended product, andby mass spectrum analysis, it was confirmed that it had an m/e value of464 with respect to a molecular weight of 464.

Synthesis of Intermediate 6

Intermediate 5 (1.4 g, 3.0 mmol) was dissolved in dichloromethane (150mL), dichloromethane solution of 1 M BBr₃(15 mL, 15 mmol) was addedthereto, and the mixture was refluxed for 8 hours. After completion ofthe reaction, ice water (50 mL) was added, and the precipitate wasfiltered off. This solid was washed with methanol, whereby obtaining awhite solid (1.4 g). The obtained solid was Intermediate 6, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 436 with respect to a molecular weight of 436.

Synthesis of Intermediate 7

Intermediate 6 (1.4 g, 3.2 mmol) was suspended in dichloromethane (75mL) and pyridine (75 mL), anhydrous triflate (3.8 mL, 22.5 mmol) wasadded thereto, and the mixture was stirred for 8 hours. After completionof the reaction, water (50 mL) was added, and the precipitate wasfiltered off. This solid was washed with methanol and ethyl acetate,whereby obtaining a white solid (1.8 g, yield: 72%). The obtained solidwas Intermediate 7, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 700 with respectto a molecular weight of 700.

Synthesis of BD-4

Under an argon atmosphere, Intermediate 7 (1.00 g, 1.43 mmol),4-iPr-N-phenylaniline (754 mg, 3.57 mmol),tris(dibenzylideneacetone)dipalladium(0) (Pd₂(dba)₃, 26 mg, 0.029 mmol),and di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (40 mg,0.11 mmol) were dissolved in xylene (120 mL), tetrahydrofuran solutionof 1 M lithium bis(trimethylsilyl)amide (3.6 mL, 3.6 mmol) was addedthereto, and the mixture was refluxed for 8 hours.

After completion of the reaction, the mixture was filtered throughcelite, and the solvent was distilled off. The obtained solid waspurified by column chromatography, whereby obtaining a yellow solid (300mg, yield: 26%). The obtained solid was BD-4, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 823 with respect to a molecular weight of 823.

Example 2-3

Compound BD-5 was synthesized by the following synthesis route.

Synthesis of BD-5

Under an argon atmosphere, Intermediate 7 (50 mg, 0.071 mmol),2-biphenylboronic acid (113 mg, 0.571 mmol), Pd₂(dba)₃ (2.6 mg, 0.0028mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 4.7 mg,0.011 mmol) and K₃PO₄ (151 mg, 0.714 mmol) were dissolved in toluene (3mL) and dioxane (3 mL) and the mixture was stirred with heating at 90°C. for 6 hours. After completion of the reaction, heated chlorobenzenewas added, the mixture was filtered through celite, and the solvent wasdistilled off. The obtained solid was washed with dimethoxyethane,whereby obtaining a yellow solid (18.5 mg, yield: 37%). The obtainedsolid was BD-5, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 708 with respectto a molecular weight of 708.

Example 2-4

Compound BD-6 was synthesized by the following synthesis route.

Synthesis of Intermediate 8

Under an argon atmosphere, 2-chloroaniline (10.0 g, 46.2 mmol),3-bromo-4-chlorobenzonitrile (5.89 g, 46.2 mmol),(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)(allyl)palladiumchloride (352 mg, 0.462 mmol) and sodium tert-butoxide (4.44 g, 46.2mmol) were suspended in dioxane (250 mL), and the mixture was stirredwith heating at 100° C. for 8 hours. After completion of the reaction,the mixture was filtered through celite and the solvent was distilledoff. The obtained residue was purified by column chromatography, wherebyobtaining a white solid (6.8 g, yield: 56%). The obtained solid wasIntermediate 8, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 263 with respectto a molecular weight of 263.

Synthesis of Intermediate 9

Under an argon atmosphere, Intermediate 8 (6.50 g, 24.7 mmol), palladiumacetate (277 mg, 1.24 mmol), tricyclohexylphosphonium tetrafluoroborate(910 mg, 2.47 mmol), and potassium carbonate (K₂CO₃, 6.83 g, 49.4 mmol)were suspended in N,N-dimethylacetamide (DMA, 250 mL), and the mixturewas stirred with heating at 140° C. for 5 hours. After completion of thereaction, the mixture was filtered through celite and the solvent wasdistilled off. The obtained residue was purified by columnchromatography, whereby obtaining a white solid (2.5 g, yield: 45%). Theobtained solid was Intermediate 9, which is an intended product, and bymass spectrum analysis, it was confirmed that it had an m/e value of 226with respect to a molecular weight of 226.

Synthesis of Intermediate 10

Under an argon atmosphere, Intermediate 9 (1.30 g, 5.74 mmol),bis(pinacolato)diboron (2.91 g, 11.5 mmol), Pd₂(dba)₃ (105 mg, 0.115mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos,0.219 g, 0.459 mmol) and potassium acetate (1.69 g, 17.2 mmol) weredissolved in dioxane (250 mL), and the mixture was stirred with heatingat 100° C. for 5 hours. After completion of the reaction, the solventwas distilled off through a short pass column chromatography, and theobtained residue was recrystallized with hexane, whereby obtaining awhite solid (1.52 g, yield: 83%). The obtained solid was Intermediate10, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 318 with respect to a molecularweight of 318.

Synthesis of Intermediate 11

Under an argon atmosphere, dibromodiiodobenzene (400 mg, 0.820 mmol),Intermediate 10 (535 mg, 1.68 mmol), Pd(PPh₃)₄ (47 mg, 0.041 mmol) andpotassium phosphate (1.05 g, 4.92 mmol) were dissolved indimethoxyethane (80 mL) and water (20 mL), and the mixture was stirredwith heating at 50° C. for 24 hours. After completion of the reaction,the precipitate was filtered off. This solid was washed with water andmethanol, whereby obtaining a white solid (365 mg, yield: 72%). Theobtained solid was Intermediate 11, which is an intended product, and bymass spectrum analysis, it was confirmed that it had an m/e value of 616with respect to a molecular weight of 616.

Synthesis of BD-6

Under an argon atmosphere, Intermediate 11 (150 mg, 0.243 mmol), Cul (9mg, 0.05 mmol), 1,10-phenanthroline monohydrate (48 mg, 0.24 mmol) andK₂CO₃ (135 mg, 0.974 mmol) were suspended in dimethylsulfoxide (20 mL),and the mixture was stirred with heating at 150° C. for 8 hours. Aftercompletion of the reaction, the precipitated solid was filtered off.This solid was washed with methanol and ethyl acetate, whereby obtaininga yellow solid (50 mg, yield: 45%). The obtained solid was BD-6, whichis an intended product, and by mass spectrum analysis, it was confirmedthat it had an m/e value of 454 with respect to a molecular weight of454.

Example 2-5

Compound GD-1 was synthesized by the following synthesis route.

Synthesis of Intermediate 12

Under an argon atmosphere, 2,6-dibromo-9,10-bis(2-naphthyl)anthracene(3.30 g, 5.61 mmol), 3,6-di-tert-butyl-1-chloro-9H-carbazole (3.70 g,11.8 mmol), palladium acetate (63 mg, 0.28 mmol),tri-tert-butylphosphonium tetrafluoroborate (163 mg, 0.561 mmol) andsodium tert-butoxide (2.16 g, 22.4 mmol) were suspended in toluene (80mL), and the mixture was stirred with heating at 100° C. for 8 hours.After completion of the reaction, the mixture was filtered throughcelite and the solvent was distilled off. The obtained residue waspurified by column chromatography, whereby obtaining a yellow solid(3.95 g, yield: 67%). The obtained solid was Intermediate 12, which isan intended product, and by mass spectrum analysis, it was confirmedthat it had an m/e value of 1054 with respect to a molecular weight of1054.

Synthesis of GD-1

Under an argon atmosphere, Intermediate 12 (3.50 g, 3.32 mmol),palladium acetate (37 mg, 0.166 mmol), tricyclohexylphosphoniumtetrafluoroborate (122 mg, 0.332 mmol) and potassium carbonate (1.84 g,13.3 mmol) was suspended in N,N-dimethylacetamide (170 mL), and themixture was stirred with heating at 140° C. for 8 hours. Aftercompletion of the reaction, the precipitate was filtered off. This solidwas washed with heated chlorobenzene, whereby obtaining an orange solid(2.1 g, yield: 65%). The obtained solid was GD-1, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 981 with respect to a molecular weight of 981.

Example 2-6

Compound BD-7 was synthesized by the following synthesis route.

Synthesis of Intermediate 13

7-Bromo-1H-indole (10.0 g, 51.0 mmol) and benzaldehyde (5.41 g, 51.0mmol) were dissolved in acetonitrile (200 mL), 57% hydroiodic acid (2mL) was added dropwise with stirring, and the mixture was stirred withheating at 80° C. for 8 hours. After completion of the reaction, theprecipitated solid was filtered off and washed with acetonitrile,whereby obtaining a pale-yellow solid (4.60 g, yield: 32%). The obtainedsolid was Intermediate 13, which is an intended product, and by massspectrum analysis, it was confirmed that it had an m/e value of 568 withrespect to a molecular weight of 568.

Synthesis of Intermediate 14

Intermediate 13 (4.50 g, 7.92 mmol) was suspended in acetonitrile and2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 4.49 g, 19.8 mmol) wasadded with stirring, and the mixture was stirred with heating at 80° C.for 6 hours. After completion of the reaction, the precipitate wasfiltered off. This solid was washed with acetonitrile, whereby obtaininga yellow solid (4.02 g, yield: 90%). The obtained solid was Intermediate14, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 566 with respect to a molecularweight of 566.

Synthesis of Intermediate 15

Under an argon atmosphere, Intermediate 14 (1.50 g, 2.65 mmol),2-chlorophenylboronic acid (1.24 g, 7.95 mmol), Pd(PPh₃)₄ (153 mg, 0.132mmol) and potassium carbonate (2.20 g, 15.9 mmol) were dissolved indimethoxyethane (20 mL) and water (5 mL), and the mixture was stirredwith heating at 80° C. for 8 hours. After completion of the reaction,the precipitate was filtered off. This solid was suspended in toluenewith heating and washed, whereby obtaining a pale-yellow solid (1.00 g,yield: 60%). The obtained solid was Intermediate 15, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 629 with respect to a molecular weight of 629.

Synthesis of BD-7

Under an argon atmosphere, Intermediate 15 (900 mg, 1.43 mmol), Cul (136mg, 0.715 mmol), 1,10-phenanthroline monohydrate (142 mg, 0.715 mmol)and K₂CO₃ (790 mg, 5.72 mmol) were suspended in N,N-dimethylformamide(30 mL), and the mixture was stirred with heating at 150° C. for 8hours. After completion of the reaction, short pass columnchromatography was carried out. After distilling off the solvent, theobtained solid was recrystallized with cyclohexanone, whereby obtaininga yellow solid (505 mg, yield: 63%). The obtained solid was BD-7, whichis an intended product, and by mass spectrum analysis, it was confirmedthat it had an m/e value of 556 with respect to a molecular weight of556.

Example 2-7

Compound BD-8 was synthesized by the following synthesis route.

Synthesis of Intermediate 16

3,6-di-tert-butyl-9H-carbazole (15.0 g, 53.7 mmol),1-bromo-2-fluorobenzene (18.8 g, 107 mmol) and cesium carbonate (35.0 g,107 mmol) were suspended in N,N-dimethylformamide (190 mL), and themixture was stirred with heating at 150° C. for 22 hours. Aftercompletion of the reaction, water was added and the precipitate wasfiltered off. This solid was purified by column chromatography, wherebyobtaining a white solid (21.7 g, yield: 93%). The obtained solid wasIntermediate 16, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 434 with respectto a molecular weight of 434.

Synthesis of Intermediate 17

Under an argon atmosphere, Intermediate 16 (21.7 g, 50.0 mmol),allylchloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(570 mg, 0.996 mmol) and potassium carbonate (13.8 g, 100 mmol) wassuspended in N,N-dimethylacetamide (250 mL), and the mixture was stirredwith heating at 130° C. for 11 hours. After completion of the reaction,water was added and the precipitate was filtered off. This solid waspurified by column chromatography, whereby obtaining a white solid (15.5g, yield: 88%). The obtained solid was Intermediate 17, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 353 with respect to a molecular weight of 353.

Synthesis of Intermediate 18

Intermediate 17 (4.10 g, 11.6 mmol) was dissolved inN,N-dimethylformamide, N-bromosuccinimide (NBS, 2.20 g, 12.36 mmol) wasadded with stirring, and the mixture was stirred at room temperature for10 hours. After completion of the reaction, the precipitate was filteredoff. This solid was purified by column chromatography, whereby obtaininga white solid (4.87 g, yield: 97%). The obtained solid was Intermediate18, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 432 with respect to a molecularweight of 432.

Synthesis of Intermediate 19

2,2,6,6-tetramethylpiperidine (3.20 g, 22.7 mmol) was dissolved intetrahydrofuran, and n-butyllithium hexane solution (1.55 M, 14.6 mL)was added with stirring at −50° C. to obtain lithiumtetramethylpiperidide (LiTMP). After stirring at the same temperaturefor 20 minutes, it was cooled to −73° C. and triisopropyl borate (8.00mL, 34.7 mmol) was added. After stirring this solution for 5 minutes, atetrahydrofuran solution of Intermediate 18 (4.83 g, 11.2 mmol) (30 mL)was added dropwise. After stirring for 10 hours while gradually raisingthe temperature to room temperature, 10% hydrochloric acid (100 mL) wasadded and the mixture was stirred for 30 minutes. After the completionof the reaction, ethyl acetate was added for extraction, and the organiclayer was collected and the solvent was distilled off. The obtainedresidues were purified by column chromatography, whereby obtaining ayellow solid (3.62 g, yield: 68%). The obtained solid was Intermediate19, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 476 with respect to a molecularweight of 476.

Synthesis of Intermediate 20

Under an argon atmosphere, 4-tert-butyl-2,6-diiodoaniline (1.39 g, 3.47mmol), Intermediate 19 (3.62 g, 7.60 mmol), Pd(PPh₃)₄ (400 mg, 0.346mmol) and sodium bicarbonate (2.30 g, 27.4 mmol) were dissolved indimethoxyethane (50 mL) and water (25 mL), and the mixture was stirredwith heating at 80° C. for 10 hours. After completion of the reaction,the mixture was extracted with methylene chloride, and the organic layerwas dried with magnesium sulfate. The solid was removed by filtration,and the solvent was distilled off. The obtained residue was purified bycolumn chromatography, whereby obtaining a yellow solid (2.41 g, yield:69%). The obtained solid was Intermediate 20, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 1010 with respect to a molecular weight of 1010.

Synthesis of BD-8

Under an argon atmosphere, Intermediate 20 (2.41 g, 2.39 mmol),Pd₂(dba)₃ (90 mg, 0.098 mmol), SPhos (16 mg, 0.39 mmol) and cesiumcarbonate (4.7 g, 14.4 mmol) was suspended in xylene (240 mL), and themixture was stirred with heating at 140° C. for 10 hours. Aftercompletion of the reaction, the precipitated solid was filtered off andwashed with water and methanol. This solid was purified by columnchromatography, whereby obtaining a yellow solid (1.24 g, yield: 61%).The obtained solid was BD-8, which is an intended product, and by massspectrum analysis, it was confirmed that it had an m/e value of 848 withrespect to a molecular weight of 848.

Example 2-8

Compound BD-9 was synthesized by the following synthesis route.

Synthesis of Intermediate 21

Under an argon atmosphere, 1-bromo-2-chloro-4-iodobenzene (17.0 g, 53.6mmol), diphenyl amine (9.07 g, 53.6 mmol), Pd₂(dba)₃ (981 mg, 1.07mmol), 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (XantPhos, 1.24g, 2.14 mmol), and NaOt-Bu (5.15 g, 53.6 mmol) were refluxed in toluene(500 mL) for 8 hours. After completion of the reaction, the mixture wasfiltered through celite, and concentrated. The obtained residue waspurified by silica gel column chromatography, whereby a white solid wasobtained (13.6 g, yield: 71%). The obtained solid was Intermediate 21,which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 359 with respect to a molecularweight of 358.6.

Synthesis of Intermediate 22

Under an argon atmosphere, Intermediate 21 (13.6 g, 38.0 mmol),bis(pinacolato)diboron (19.3 g, 76.0 mmol), PdCl₂(dppf) (621 mg, 0.761mmol), and potassium acetate (7.46 g, 76 mmol) were suspended in dioxane(400 mL) and refluxed for 7 hours. After completion of the reaction, thesolvent was concentrated by passing through short pass silica gel columnchromatography. The obtained solid was washed with methanol, whereby awhite solid was obtained (18.5 mg, yield: 71%). The obtained solid wasIntermediate 22, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 406 with respectto a molecular weight of 405.7.

Synthesis of Intermediate 23

Under an argon atmosphere, dibromo-modification (Intermediate 14) (5.00g, 8.83 mmol), a boronic acid ester (Intermediate 22) (10.8 g, 26.5mmol), and Pd(PPh₃)₄ (1.02 g, 0.883 mmol) were dissolved in toluene (250mL) and dimethylsulfoxide (500 mL), and 2 M Na₂CO₃ (130 mL) was addedthereto, and the mixture was stirred with heating at 100° C. for 6hours. After completion of the reaction, the solvent was concentrated bypassing through short pass silica gel column chromatography. Theobtained residue was washed with ethyl acetate and toluene, whereby ayellow solid was obtained (6.39 g, yield: 75%). The obtained solid wasIntermediate 23, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 965 with respectto a molecular weight of 964.0.

Synthesis of BD-9

Under argon atmosphere, Intermediate 23 (6.24 g, 6.47 mmol), copper(I)iodide (1.48 g, 7.77 mmol), 1,10-phenanthroline (1.40 g, 7.77 mmol), andpotassium carbonate (7.16 g, 51.8 mmol) were suspended inN,N-dimethylacetamide (1.2 L), and the mixture was stirred with heatingat 120° C. for 15 hours. After completion of the reaction, the solventwas concentrated by passing through short pass silica gel columnchromatography. The obtained residue was recrystallized withchlorobenzene and washed with toluene and methanol, whereby a yellowsolid was obtained (4.54 g, yield: 79%). The obtained solid was BD-9,which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 892 with respect to a molecularweight of 891.1.

Example 2-9

Compound BD-10 was synthesized by the following synthesis route.

Synthesis of Intermediate 24

Under an argon atmosphere, 4-tert-butyl-2-iodoaniline (2.00 g, 7.27mmol), Intermediate 19 (3.00 g, 6.30 mmol), Pd (PPh₃)₄(420 mg, 0.364mmol), and sodium hydrogen carbonate (1.90 g, 22.6 mmol) were dissolvedin dimethoxyethane (40 mL) and water (20 mL), and the mixture wasstirred with heating at 80° C. for 10 hours. After completion of thereaction, the mixture was extracted with methylene chloride, and theorganic phase was dried with magnesium sulfate. The solid was removed byfiltration, and the solvent was distilled off. The obtained residue waspurified by column chromatography, whereby obtaining a white solid (2.95g, yield: 81%). The obtained solid was Intermediate 24, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 580 with respect to a molecular weight of 579.6.

Synthesis of Intermediate 25

Intermediate 24 (2.95 g, 5.09 mmol) was dissolved in methylene chloride(50 mL) and methanol (20 mL), and calcium carbonate (0.80 g, 8.0 mmol)and benzyltrimethylammonium dichloro iodide (1.80 g, 5.17 mmol) wereadded with stirring, and the mixture was stirred at room temperature for10 hours. After completion of the reaction, a saturated aqueous sodiumthiosulfate solution was added, the mixture was slightly stirred, andthen extracted with methylene chloride. The organic phase wasconcentrated and the obtained solid was purified by columnchromatography, whereby obtaining a white solid (3.16 g, yield: 88%).The obtained solid was Intermediate 25, which is an intended product,and by mass spectrum analysis, it was confirmed that it had an m/e valueof 706 with respect to a molecular weight of 705.5.

Synthesis of Intermediate 26

Under an argon atmosphere, iodine intermediate (Intermediate 25) (3.16g, 4.48 mmol), boronic acid compound A (2.00 g, 5.43 mmol), Pd(PPh₃)₄(260 mg, 0.225 mmol), and sodium hydrogen carbonate (1.60 g, 19.1 mmol)were dissolved in dimethoxyethane (40 mL) and water (20 mL), and themixture was stirred with heating at 80° C. for 10 hours. Aftercompletion of the reaction, extraction was performed with methylenechloride, and the organic phase was dried over magnesium sulfate. Thesolid was removed by filtration, and the solvent was distilled off. Theobtained residue was purified by column chromatography, wherebyobtaining a yellow solid (3.93 g, yield 97%). The obtained solid wasIntermediate 26, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 902 with respectto a molecular weight of 901.8.

Synthesis of BD-10

Under argon atmosphere, Intermediate 26 (3.93 g, 2.39 mmol), Pd₂(dba)₃(160 mg, 0.175 mmol), SPhos (290 mg, 0.706 mmol), and cesium carbonate(8.4 g, 26 mmol) were suspended in xylene (360 mL), and the mixture wasstirred with heating at 140° C. for 10 hours. After completion of thereaction, the precipitated solid was filtered off and washed with waterand methanol. This solid was purified by column chromatography, wherebyobtaining a yellow solid (1.35 g, yield: 42%). The obtained solid wasBD-10, which is an intended product, and by mass spectrum analysis, itwas confirmed that it had an m/e value of 741 with respect to amolecular weight of 740.0.

Example 2-10

Compound BD-11 was synthesized by the following synthesis route.

Synthesis of Intermediate 27

Under argon atmosphere, Compound B (3.00 g, 6.94 mmol),4-tert-butyl-aniline (1.20 g, 8.04 mmol), Pd₂(dba)₃ (60 mg, 0.066 mmol),tri-tert-butyl phosphonium tetrafluoroborate (80 mg, 0.276 mmol), andsodium tert-butoxide (0.94 g, 9.8 mmol) were suspended in toluene (25mL), and the mixture was stirred with heating at 100° C. for 10 hours.After completion of the reaction, the mixture was filtered throughcelite and the solvent was distilled off. The obtained residue waspurified by column chromatography, whereby obtaining a yellow solid(3.20 g, yield: 92%). The obtained solid was Intermediate 27, which isan intended product, and by mass spectrum analysis, it was confirmedthat it had an m/e value of 508 with respect to a molecular weight of500.7.

Synthesis of Intermediate 28

Intermediate 27 (3.20 g, 6.39 mmol) was dissolved inN,N-dimethylformamide (20 mL), and about 60% sodium hydride (0.77 g, 19mmol) dispersed in liquid paraffin was added thereto, and the mixturewas stirred for 20 minutes. 1,3-dichloro-2-fluorobenzene (1.6 g, 9.7mmol) was added to this solution and the mixture was stirred withheating at 50° C. for 10 hours. After completion of the reaction, theprecipitated solid was filtered off and washed with methanol. This solidwas purified by column chromatography, whereby obtaining a yellow solid(3.44 g, yield: 79%). The obtained solid was Intermediate 28, which isan intended product, and by mass spectrum analysis, it was confirmedthat it had an m/e value of 646 with respect to a molecular weight of645.7.

Synthesis of BD-11

Under argon atmosphere, Intermediate 28 (3.44 g, 5.33 mmol),allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(120 mg, 0.210 mmol), and potassium carbonate (2.94 g, 21.5 mmol) weresuspended in N,N-dimethylacetamide (30 mL), and the mixture was stirredwith heating at 150° C. for 10 hours. After completion of the reaction,water was added and the solid was filtered off. The obtained solid waspurified by column chromatography and recrystallization, wherebyobtaining a yellow solid (1.87 g, yield 61%). The obtained solid wasBD-11, which is an intended product, and by mass spectrum analysis, itwas confirmed that it had an m/e value of 573 with respect to amolecular weight of 572.8.

Example 2-11

Compound BD-12 was synthesized by the following synthesis route.

Synthesis of Intermediate 29

Under argon atmosphere, Intermediate 7 (3.00 g, 4.28 mmol),2-(ethoxycarbonyl) phenylboronic acid (2.50 g, 12.9 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (157 mg, 0.214mmol), and potassium carbonate (2.37 g, 17.1 mmol) were suspended inN,N-dimethylformamide (200 mL), and the mixture was stirred with heatingat 130° C. for 8 hours. After completion of the reaction, water wasadded and the precipitate was filtered off and washed with methanol. Theobtained solid was purified by column chromatography, whereby obtaininga yellow solid (2.40 g, yield: 80%). The obtained solid was Intermediate29, which is an intended product, and by mass spectrum analysis, it wasconfirmed that it had an m/e value of 701 with respect to a molecularweight of 700.8.

Synthesis of Intermediate 30

Under an argon atmosphere, Intermediate 29 (2.35 g, 3.35 mmol) wasdissolved in tetrahydrofuran (300 mL), and 1 M phenylmagnesiumbromide/THF solution (30 mL, 30 mmol) was added dropwise at 0° C. Aftercompletion of the dropwise addition, the mixture was heated to roomtemperature and stirred for 5 hours. After completion of the reaction,water was added and extraction was performed with ethyl acetate. Theorganic layer was concentrated and the obtained solid was purified bycolumn chromatography, whereby obtaining a yellow solid (2.10 g, yield:68%). The obtained solid was Intermediate 30, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 922 with respect to a molecular weight of 921.1.

Synthesis of BD-12

Acetic acid (50 mL) and concentrated hydrochloric acid (3 mL) were addedto Intermediate 30 (2.00 g, 2.17 mmol), and the mixture was stirred withheating at 100° C. for 6 hours. After completion of the reaction, waterwas added and the solid was filtered off. The obtained solid waspurified by column chromatography, whereby obtaining a yellow solid(0.82 g, yield 43%). The obtained solid was BD-12, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 886 with respect to a molecular weight of 885.1.

Example 2-12

Compound BD-13 was synthesized by the following synthesis route.

Synthesis of Intermediate 31

Under an argon atmosphere, dibromo-modification (Intermediate 13) (500mg, 0.88 mmol), boronic acid compound C (380 mg, 1.85 mmol), andPd(PPh₃)₄ (40 mg, 0.035 mmol) were dissolved in toluene (5 mL) anddimethylsulfoxide (10 mL), and 2 M Na₂CO₃ (2 mL) was added thereto, andthe mixture was stirred with heating at 80° C. for 6 hours. Aftercompletion of the reaction, the solvent was concentrated by passingthrough short pass silica gel column chromatography. The obtainedresidue was washed with ethyl acetate and toluene, whereby a yellowsolid was obtained (320 mg, yield: 50%). The obtained solid wasIntermediate 31, which is an intended product, and by mass spectrumanalysis, it was confirmed that it had an m/e value of 730 with respectto a molecular weight of 729.7.

Synthesis of BD-13

Under argon atmosphere, Intermediate 31 (300 mg, 0.411 mmol), copper (I)iodide (94 mg, 0.49 mmol), 1,10-phenanthroline (89 mg, 0.49 mmol), andpotassium carbonate (450 mg, 3.29 mmol) were suspended inN,N-dimethylacetamide (20 mL), and the mixture was stirred with heatingat 120° C. for 15 hours. After completion of the reaction, the solventwas concentrated by passing through short pass silica gel columnchromatography. The obtained residue was washed with toluene andmethanol, whereby a yellow solid was obtained (148 mg, yield: 55%). Theobtained solid was BD-13, which is an intended product, and by massspectrum analysis, it was confirmed that it had an m/e value of 657 withrespect to a molecular weight of 656.8.

Example 2-13

Compound BD-14 was synthesized by the following synthesis route.

Synthesis of Intermediate 32

Under argon atmosphere, 3,6-di-tert-butyl-9H-carbazole (11.6 g, 41.5mmol), 1-bromo-2-fluoro-4-iodobenzene (25 g, 83 mmol), and cesiumcarbonate (27 g, 83 mmol) were suspended in N,N-dimethylformamide (145mL), and the mixture was stirred with heating at 150° C. for 22 hours.After completion of the reaction, water was added and the precipitatewas filtered off. The obtained solid was purified by columnchromatography, whereby obtaining a white solid (21.5 g, yield: 92%).The obtained solid was Intermediate 32, which is an intended product,and by mass spectrum analysis, it was confirmed that it had an m/e valueof 561 with respect to a molecular weight of 560.3.

Synthesis of Intermediate 33

Under argon atmosphere, Intermediate 32 (5.00 g, 8.92 mmol),bis(pinacolato)diboron (3.40 g, 13.4 mmol), palladium acetate (40 mg,0.18 mmol), triphenylphosphine (50 mg, 0.19 mmol), copper iodide (0.34g, 1.79 mmol), and cesium carbonate (4.4 g, 13.5 mmol) were suspended inacetonitrile (50 mL), and the mixture was stirred at room temperaturefor 20 hours. After completion of the reaction, the mixture was filteredthrough celite and the solvent was concentrated. The obtained solid waspurified by column chromatography, whereby obtaining a white solid (3.84g, yield: 77%). The obtained solid was Intermediate 33, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 561 with respect to a molecular weight of 560.4.

Synthesis of Intermediate 34

Under an argon atmosphere, iodine intermediate 32 (3.49 g, 6.23 mmol),boronic acid intermediate 33 (3.84 g, 6.85 mmol), Pd(PPh₃)₄ (360 mg,0.312 mmol), and potassium carbonate (2.60 g, 18.8 mmol) were dissolvedin tetrahydrofuran (90 mL) and water (20 mL), and the mixture wasstirred with heating at 80° C. for 10 hours. After completion of thereaction, extraction was performed with methylene chloride, and theorganic layer was dried over magnesium sulfate. The solid was removed byfiltration, and the solvent was distilled off. The obtained residue waspurified by column chromatography, whereby obtaining a white solid (5.33g, yield 99%). The obtained solid was Intermediate 34, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 867 with respect to a molecular weight of 866.8.

Synthesis of Intermediate 35

Under argon atmosphere, Intermediate 34 (5.33 g, 6.15 mmol),allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(140 mg, 0.245 mmol), and potassium carbonate (3.40 g, 24.6 mmol) weresuspended in N,N-dimethylacetamide (30 mL), and the mixture was stirredwith heating at 130° C. for 11 hours. After completion of the reaction,water was added and the precipitate was filtered off. The obtained solidwas purified by column chromatography, whereby obtaining a yellow solid(3.0 g, yield: 69%). The obtained solid was Intermediate 35, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 706 with respect to a molecular weight of 705.0.

Synthesis of Intermediate 36

Intermediate 35 (3.00 g, 4.26 mmol) was dissolved in N,N-dimethylformamide (50 mL) and methylene chloride (150 mL), andN-bromosuccinimide (1.67 g, 9.38 mmol) was added with stirring, and themixture was stirred at room temperature for 11 hours. After completionof the reaction, methylene chloride was distilled off, and water wasadded thereto, and the solid was filtered off. The obtained solid waspurified by column chromatography, whereby obtaining a white solid (3.51g, yield: 95%). The obtained solid was Intermediate 36, which is anintended product, and by mass spectrum analysis, it was confirmed thatit had an m/e value of 863 with respect to a molecular weight of 862.8.

Synthesis of BD-14

Under argon atmosphere, Intermediate 36 (3.50 g, 4.06 mmol), Pd₂(dba)₃(190 mg, 0.207 mmol), tri-tert-butylphosphonium tetrafluoroborate (240mg, 0.828 mmol), and sodium tert-butoxide (1.56 g, 16.3 mmol) weresuspended in toluene (40 mL), and aniline (0.37 mL, 4.1 mmol) was addedthereto. The mixture was stirred with heating at 80° C. for 22 hours.After completion of the reaction, the precipitated solid was filteredand washed with toluene and methanol, whereby obtaining a yellow solid(2.46 g, yield: 76%). The obtained solid was BD-14, which is an intendedproduct, and by mass spectrum analysis, it was confirmed that it had anm/e value of 795 with respect to a molecular weight of 794.1.

Several embodiments and/or examples of the present invention have beendescribed in detail above. However, without substantially departing fromnovel teachings and effects of the present invention, the person skilledin the art can readily make a number of modifications to the embodimentsand/or examples which are exemplifications of these teachings andeffects. Thus, these modifications are included in the scope of thepresent invention.

The documents described in this specification and the contents of theapplication that serves as the basis of priority claim under Parisconvention are incorporated herein by reference in its entirety.

1. A compound represented by the following formulas (3), (4) or (5):

wherein in the formulas (3), (4) and (5), the ring A′ is a substitutedor unsubstituted fused aryl ring including 10 to 50 ring carbon atoms ora substituted or unsubstituted fused heterocycle including 8 to 50 ringatoms; one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ toR₁₆ may form a substituted or unsubstituted, saturated or unsaturatedring; R₁ to R₇ and R₁₀ to R₁₆ that do not form the substituted orunsubstituted, saturated or unsaturated ring are independently ahydrogen atom, a substituted or unsubstituted alkyl group including 1 to50 carbon atoms, a substituted or unsubstituted haloalkyl groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted alkenylgroup including 2 to 50 carbon atoms, a substituted or unsubstitutedalkynyl group including 2 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, asubstituted or unsubstituted alkoxy group including 1 to 50 carbonatoms, a substituted or unsubstituted alkylthio group including 1 to 50carbon atoms, a substituted or unsubstituted aryloxy group including 6to 50 ring carbon atoms, a substituted or unsubstituted arylthio groupincluding 6 to 50 ring carbon atoms, a substituted or unsubstitutedaralkyl group including 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃),—C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitrogroup, a substituted or unsubstituted aryl group including 6 to 50 ringcarbon atoms or a substituted or unsubstituted monovalent heterocyclicgroup including 5 to 50 ring atoms; R₁₇ is a hydrogen atom, asubstituted or unsubstituted alkyl group including 1 to 50 carbon atoms,a substituted or unsubstituted haloalkyl group including 1 to 50 carbonatoms, a substituted or unsubstituted alkenyl group including 2 to 50carbon atoms, a substituted or unsubstituted alkynyl group including 2to 50 carbon atoms, a substituted or unsubstituted cycloalkyl groupincluding 3 to 50 ring carbon atoms, a substituted or unsubstitutedalkoxy group including 1 to 50 carbon atoms, a substituted orunsubstituted alkylthio group including 1 to 50 carbon atoms, asubstituted or unsubstituted aryloxy group including 6 to 50 ring carbonatoms, a substituted or unsubstituted arylthio group including 6 to 50ring carbon atoms, a substituted or unsubstituted aralkyl groupincluding 7 to 50 carbon atoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅,—N(R₃₆)(R₃₇), a halogen atom, a cyano group, a nitro group, asubstituted or unsubstituted aryl group including 6 to 50 ring carbonatoms or a substituted or unsubstituted monovalent heterocyclic groupincluding 5 to 50 ring atoms; two R₁₇s may be the same as or differentfrom each other; R₃₁ to R₃₇ are independently a hydrogen atom, asubstituted or unsubstituted alkyl group including 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group including 3 to 50 ringcarbon atoms, a substituted or unsubstituted aryl group including 6 to50 ring carbon atoms or a substituted or unsubstituted monovalentheterocyclic group including 5 to 50 ring atoms; and when a plurality ofeach of R₃₁ to R₃₇ is present, the plurality of each of R₃₁s to R₃₇s maybe the same as or different from each other.
 2. The compound accordingto claim 1, wherein the substituted or unsubstituted fused aryl ringincluding 10 to 50 ring carbon atoms is a substituted or unsubstitutednaphthalene ring, a substituted or unsubstituted anthracene ring or asubstituted or unsubstituted fluorene ring, and the substituted orunsubstituted fused heterocycle including 8 to 50 ring atoms is asubstituted or unsubstituted dibenzofuran ring, a substituted orunsubstituted carbazole ring or a substituted or unsubstituteddibenzothiophene ring.
 3. The compound according to claim 1, wherein thesubstituted or unsubstituted fused aryl ring including 10 to 50 ringcarbon atoms is a substituted or unsubstituted naphthalene ring or asubstituted or unsubstituted fluorene ring, and the substituted orunsubstituted fused heterocycle including 8 to 50 ring atoms is asubstituted or unsubstituted dibenzofuran ring, a substituted orunsubstituted carbazole ring or a substituted or unsubstituteddibenzothiophene ring.
 4. The compound according to claim 1, beingselected from the group consisting of compounds represented by thefollowing formulas (6-1) to (6-6):

wherein in the formulas (6-1) to (6-6), R₁ to R₇ and R₁₀ to R₁₇ are asdefined in the formulas (3), (4) and (5); X is O, NR₂₅ or C(R₂₆)(R₂₇);one or more pairs of adjacent two or more of R₂₁ to R₂₇ may form asubstituted or unsubstituted, saturated or unsaturated ring; R₂₁ to R₂₇that do not form the substituted or unsubstituted, saturated orunsaturated ring are independently a hydrogen atom, a substituted orunsubstituted alkyl group including 1 to 50 carbon atoms, a substitutedor unsubstituted haloalkyl group including 1 to 50 carbon atoms, asubstituted or unsubstituted alkenyl group including 2 to 50 carbonatoms, a substituted or unsubstituted alkynyl group including 2 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group including3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 50 carbon atoms, a substituted or unsubstitutedaryloxy group including 6 to 50 ring carbon atoms, a substituted orunsubstituted arylthio group including 6 to 50 ring carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 carbonatoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogenatom, a cyano group, a nitro group, a substituted or unsubstituted arylgroup including 6 to 50 ring carbon atoms or a substituted orunsubstituted monovalent heterocyclic group including 5 to 50 ringatoms; and R₃₁ to R₃₇ are as defined in the formulas (3), (4) and (5).5. The compound according to claim 1, wherein R₁ to R₇ and R₁₀ to R₁₇are independently selected from the group consisting of a hydrogen atom,a substituted or unsubstituted aryl group including 6 to 50 ring carbonatoms and a substituted or unsubstituted heterocyclic group including 5to 50 ring atoms.
 6. The compound according to claim 1, wherein R₁ to R₇and R₁₀ to R₁₇ are independently selected from the group consisting of ahydrogen atom, a substituted or unsubstituted aryl group including 6 to18 ring carbon atoms and a substituted or unsubstituted heterocyclicgroup including 5 to 18 ring atoms.
 7. The compound according to claim1, being represented by the following formula (3-2):

wherein in the formula (3-2), R₃, R₅, R₆, R₁₀, R₁₂ and R₁₃ are asdefined in the formulas (3), (4) and (5).
 8. The compound according toclaim 1, wherein a substituent in the “substituted or unsubstituted” isselected from the group consisting of an alkyl group including 1 to 50carbon atoms, a haloalkyl group including 1 to 50 carbon atoms, aalkenyl group including 2 to 50 carbon atoms, a alkynyl group including2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 ring carbonatoms, a alkoxy group including 1 to 50 carbon atoms, a alkylthio groupincluding 1 to 50 carbon atoms, a aryloxy group including 6 to 50 ringcarbon atoms, a arylthio group including 6 to 50 ring carbon atoms, aaralkyl group including 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃),—C(═O)R₄₄, —COOR₄₅, —S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₈), —Ge(R₄₉)(R₅₀)(R₅₁),—N(R₅₂)(R₅₃), a hydroxyl group, a halogen atom, a cyano group, a nitrogroup, an aryl group including 6 to 50 ring carbon atoms, and amonovalent heterocyclic group including 5 to 50 ring atoms; R₄₁ to R₅₃are independently a hydrogen atom, an alkyl group including 1 to 50carbon atoms, an aryl group including 6 to 50 ring carbon atoms or amonovalent heterocyclic group including 5 to 50 ring atoms; and when aplurality of each of R₄₁s to R₅₃s is present, the plurality of each ofR₄₁s to R₅₃s may be the same as or different from each other.
 9. Thecompound according to claim 1, wherein a substituent in the “substitutedor unsubstituted” is an alkyl group including 1 to 50 carbon atoms, anaryl group including 6 to 50 ring carbon atoms, or a monovalentheterocyclic group including 5 to 50 ring atoms.
 10. The compoundaccording to claim 1, wherein a substituent in the “substituted orunsubstituted” is an alkyl group including 1 to 18 carbon atoms, an arylgroup including 6 to 18 ring carbon atoms, or a monovalent heterocyclicgroup including 5 to 18 ring atoms.
 11. The compound according to claim1, being represented by the following formula (3-11):

wherein in the formula (3-11), one or more pairs of adjacent two or moreof R₁ to R₇ and R₁₀ to R₁₆ may form a substituted or unsubstituted,saturated or unsaturated ring; R₁ to R₇ and R₁₀ to R₁₆ that do not formthe substituted or unsubstituted, saturated or unsaturated ring areindependently a hydrogen atom, a substituted or unsubstituted alkylgroup including 1 to 50 carbon atoms, a substituted or unsubstitutedhaloalkyl group including 1 to 50 carbon atoms, a substituted orunsubstituted alkenyl group including 2 to 50 carbon atoms, asubstituted or unsubstituted alkynyl group including 2 to 50 carbonatoms, a substituted or unsubstituted cycloalkyl group including 3 to 50ring carbon atoms, a substituted or unsubstituted alkoxy group including1 to 50 carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 50 ring carbon atoms, a substituted orunsubstituted arylthio group including 6 to 50 ring carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 carbonatoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogenatom, a cyano group, a nitro group, a substituted or unsubstituted arylgroup including 6 to 50 ring carbon atoms or a substituted orunsubstituted monovalent heterocyclic group including 5 to 50 ringatoms, provided that at least one of R₁ to R₇ and R₁₀ to R₁₆ is—N(R₃₆)(R₃₇); R₁₇ is a hydrogen atom, a substituted or unsubstitutedalkyl group including 1 to 50 carbon atoms, a substituted orunsubstituted haloalkyl group including 1 to 50 carbon atoms, asubstituted or unsubstituted alkenyl group including 2 to 50 carbonatoms, a substituted or unsubstituted alkynyl group including 2 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group including3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted alkylthiogroup including 1 to 50 carbon atoms, a substituted or unsubstitutedaryloxy group including 6 to 50 ring carbon atoms, a substituted orunsubstituted arylthio group including 6 to 50 ring carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 carbonatoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogenatom, a cyano group, a nitro group, a substituted or unsubstituted arylgroup including 6 to 50 ring carbon atoms or a substituted orunsubstituted monovalent heterocyclic group including 5 to 50 ringatoms; two R₁₇s may be the same as or different from each other; R₃₁ toR₃₇ are independently a hydrogen atom, a substituted or unsubstitutedalkyl group including 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 50 ring carbonatoms or a substituted or unsubstituted monovalent heterocyclic groupincluding 5 to 50 ring atoms; when a plurality of each of R₃₁ to R₃₇ ispresent, the plurality of each of R₃₁s to R₃₇s may be the same as ordifferent from each other.
 12. The compound according to claim 11,wherein the compound represented by the formula (3-11) is the compoundrepresented by the following formula (3-12):

wherein in the formula (3-12), one or more pairs of adjacent two or moreof R₁ to R₇ and R₁₀ to R₁₆ may form a substituted or unsubstituted,saturated or unsaturated ring; R₁ to R₇ and R₁₀ to R₁₆ that do not formthe substituted or unsubstituted, saturated or unsaturated ring areindependently a hydrogen atom, a substituted or unsubstituted alkylgroup including 1 to 50 carbon atoms, a substituted or unsubstitutedhaloalkyl group including 1 to 50 carbon atoms, a substituted orunsubstituted alkenyl group including 2 to 50 carbon atoms, asubstituted or unsubstituted alkynyl group including 2 to 50 carbonatoms, a substituted or unsubstituted cycloalkyl group including 3 to 50ring carbon atoms, a substituted or unsubstituted alkoxy group including1 to 50 carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 50 ring carbon atoms, a substituted orunsubstituted arylthio group including 6 to 50 ring carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 carbonatoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogenatom, a cyano group, a nitro group, a substituted or unsubstituted arylgroup including 6 to 50 ring carbon atoms or a substituted orunsubstituted monovalent heterocyclic group including 5 to 50 ringatoms, provided that any two of R₁ to R₇ and R₁₀ to R₁ is —N(R₃₆)(R₃₇);R₁₇ is a hydrogen atom, a substituted or unsubstituted alkyl groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted haloalkylgroup including 1 to 50 carbon atoms, a substituted or unsubstitutedalkenyl group including 2 to 50 carbon atoms, a substituted orunsubstituted alkynyl group including 2 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl group including 3 to 50 ringcarbon atoms, a substituted or unsubstituted alkoxy group including 1 to50 carbon atoms, a substituted or unsubstituted alkylthio groupincluding 1 to 50 carbon atoms, a substituted or unsubstituted aryloxygroup including 6 to 50 ring carbon atoms, a substituted orunsubstituted 170 rylthiol group including 6 to 50 ring carbon atoms, asubstituted or unsubstituted aralkyl group including 7 to 50 carbonatoms, —Si(R₃₁)(R₃₂)(R₃₃), —C(═O)R₃₄, —COOR₃₅, —N(R₃₆)(R₃₇), a halogenatom, a cyano group, a nitro group, a substituted or unsubstituted arylgroup including 6 to 50 ring carbon atoms or a substituted orunsubstituted monovalent heterocyclic group including 5 to 50 ringatoms; Two R₁₇s may be the same as or different from each other; R₃₁ toR₃₇ are independently a hydrogen atom, a substituted or unsubstitutedalkyl group including 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, asubstituted or unsubstituted aryl group including 6 to 50 ring carbonatoms or a substituted or unsubstituted monovalent heterocyclic groupincluding 5 to 50 ring atoms; and when a plurality of each of R₃₁ to R₃₇is present, the plurality of each of R₃₁s to R₃₇s may be the same as ordifferent from each other.
 13. The compound according to claim 11,wherein the compound represented by the formula (3-11) is the compoundrepresented by the following formula (3-13):

wherein in the formula (3-13), one or more pairs of adjacent two or moreof R₁ to R₄ and R₁₀ to R₁₃ may form a substituted or unsubstituted,saturated or unsaturated ring; R₁ to R₄, R₁₀ to R₁₃ and R₁₇ that do notform the substituted or unsubstituted, saturated or unsaturated ring areindependently a hydrogen atom, a substituted or unsubstituted aryl groupincluding 6 to 18 ring carbon atoms or a substituted or unsubstitutedmonovalent heterocyclic group including 5 to 18 ring atoms; two R₁₇s maybe the same as or different from each other; and R_(A), R_(B), R_(C) andR_(D) are independently a substituted or unsubstituted aryl groupincluding 6 to 18 ring carbon atoms or a substituted or unsubstitutedmonovalent heterocyclic group including 5 to 18 ring atoms.
 14. Thecompound according to claim 13, wherein the compound represented by theformula (3-13) is the compound represented by the formula (3-14):

wherein in the formula (3-14), R₁₇, R_(A), R_(B), R_(C) and R_(D) are asdefined in the formula (3-13).
 15. The compound according to claim 13,wherein R_(A), R_(B), R_(C) and R_(D) are independently a substituted orunsubstituted aryl group including 6 to 18 ring carbon atoms.
 16. Thecompound according to claim 13, wherein R_(A), R_(B), R_(C) and R_(D)are independently a substituted or unsubstituted phenyl group.
 17. Thecompound according to claim 11, wherein two R₁₇s are hydrogen atoms. 18.The compound according to claim 11, wherein a substituent in the“substituted or unsubstituted” is selected from the group consisting ofan alkyl group including 1 to 18 carbon atoms, an aryl group including 6to 18 ring carbon atoms, and a monovalent heterocyclic group including 5to 18 ring atoms.
 19. The compound according to claim 11, wherein asubstituent in the “substituted or unsubstituted” is an alkyl groupincluding 1 to 5 carbon atoms.
 20. The compound according to claim 13,wherein R_(A), R_(B), R_(C) and R_(D) are independently a substituted orunsubstituted phenyl group; and two R₁₇s are hydrogen atoms.
 21. Thecompound according to claim 13, wherein R_(A), R_(B), R_(C) and R_(D)are independently a substituted or unsubstituted phenyl group; two R₁₇sare hydrogen atoms; and a substituent in the “substituted orunsubstituted” is selected from the group consisting of an alkyl groupincluding 1 to 20 carbon atoms, an aryl group including 6 to 20 ringcarbon atoms, and a monovalent heterocyclic group including 5 to 20 ringatoms.
 22. The compound according to claim 13, wherein R_(A), R_(B),R_(C) and R_(D) are independently a substituted or unsubstituted phenylgroup; two R₁₇s are hydrogen atoms; and a substituent in the“substituted or unsubstituted” is an alkyl group including 1 to 5 carbonatoms.
 23. A material for an organic electroluminescence devicecomprising the compound according to claim
 1. 24. An organicelectroluminescence device comprising: a cathode, an anode, and at leastone organic layer disposed between the cathode and the anode, wherein atleast one layer of the at least one organic layer comprises the compoundaccording to claim
 1. 25. An electronic apparatus provided with theorganic electroluminescence device according to claim 24.